PODCAST · education
AssociationHelpNow
by Raymond Dickey
AssociationHelpNow® delivers practical, real-world conversations for community association managers and board members who live this work every day. Each episode features candid discussions, expert interviews, and timely insights covering legal, insurance, operational, leadership, and communication challenges facing HOAs and condominiums. From livestream highlights to workshop takeaways, the show bridges the gap between theory and practice—helping listeners make smarter, more confident decisions in complex environments.Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice and may have been edited.
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25 Must-Have Policies & Procedures Every HOA Should Have
Every community association operates on policies and procedures—but many boards don’t realize which ones are essential until a problem occurs. In this livestream, our industry expert panel reviews 25 must-have policies and procedures that associations should strongly consider having in place.————————————————————————CEU On-Demand: Available all day on Jun 23, 2026 at:https://attendee.gotowebinar.com/register/1325461722409362262YouTube: https://youtu.be/AiVrI72mTfA————————————————————————CEU INSTRUCTIONS: During the session, you are required to use the “Question” feature and enter “CEU” when prompted. If you cannot locate the Question feature, stop immediately and email us for instructions so we can assist you ([email protected]). You will be prompted a total of three times during the program. We must receive all required responses in order to verify your participation.————————————————————————We’ll walk through the purpose of each policy, why it matters, and how it helps boards and managers operate more consistently and fairly.You may discover that your association already has many of these in place—or you may find a few important ones missing.Times change. Communities change. Laws change. Good associations make sure their policies evolve too.Panel:John LaGumina, Esq. • The LaGumina Law Firm, PLLC • [email protected] • www.laguminalaw.comMike Luzzi, CIRMS • Acrisure • [email protected] • www.acrisure.comDavid Byrne, Esq. • Ansell Grimm & Aaron, PC • [email protected] • www.ansell.lawStephanie Harmon, CMCA, AMS, PCAM • FirstService Residential • [email protected] Kravit, Esq. • Kovitz Shifrin Nesbit • [email protected] • www.ksnlaw.comGregg V. Gerelli • Gerelli Insurance Agency, Inc. • [email protected] • www.gerelli-insurance.comRaymond Dickey • AssociationHelpNow.com • [email protected] • www.AssociationHelpNow.comThis content does not constitute professional advice.
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One-on-One with Adam Clarkson, Esq. — Real Talk on HOA Legal Risk & Decision-Making
Join us for an exclusive one-on-one conversation with Adam Clarkson, Esq., as we dig into the real-world legal challenges facing community associations today. This is not a panel—this is a focused, direct discussion designed to unpack how attorneys actually think when boards and managers are making tough calls.We’ll explore where legal risk truly begins (and where it’s often misunderstood), how boards unintentionally create exposure, and what managers should and should not be doing when legal issues start to surface. Adam will also share practical insights on communication with counsel, navigating gray areas, and how to avoid turning small issues into expensive problems.————————————————————————CEU On-Demand: Available all day on Jun 11, 2026 12:00 AM EDT at:https://attendee.gotowebinar.com/register/4407727066592917078YouTube (available now): https://youtu.be/R2Is4pkyR4A————————————————————————This session will also include an open Q&A, where viewers are encouraged to ask anything—real scenarios, gray-area questions, or situations you’re currently dealing with. Nothing is off limits, and the goal is to give you direct, practical insight you can actually use.Whether you're a manager, board member, or industry professional, this session will give you a clearer understanding of how legal strategy intersects with day-to-day operations—and how to make better decisions before issues escalate.Adam Clarkson, Esq. • Clarkson McAlonis & O’Connor, P.C. • [email protected] • www.cmolawpc.comKey Discussion Points:- Where associations unknowingly create legal risk- The biggest mistakes boards make when handling disputes- When to involve legal counsel—and when not to- How managers can protect themselves professionally- Real-world scenarios and how they should be handledThis content does not constitute professional advice.
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Things That Kill Insurance Deals: The Mistakes Boards Can’t Afford to Make
Insurance coverage is getting harder, more expensive, and more complicated for community associations — and small mistakes by boards or managers can create major problems. In this session, insurance professionals Greg Gerelli and Dawn Becker-Durnin discuss the issues that can delay, damage, or even kill insurance deals, including incomplete applications, poor documentation, deferred maintenance, claims history, rental percentages, lender requirements, underwriting red flags, and changing insurance market conditions.-------- YouTube: https://youtu.be/6ORxa-WnfO4-------- OnDemand 1h CEU Video (available all day) - Insurance Deal Killers on Jun 2, 2026 at: https://attendee.gotowebinar.com/register/9125978851478394968The discussion also explains why the right insurance agent matters, how boards can better prepare for renewals, what carriers are looking for, and why associations should not treat insurance as a simple checkbox. Viewers will learn practical steps boards can take now to improve their insurance position, avoid unnecessary surprises, and better protect their communities.Gregg V. Gerelli • Gerelli Insurance Agency, Inc. • [email protected] • www.gerelli-insurance.comDawn Becker-Durnin, CIRMS • Acrisure • [email protected] • www.acrisure.comRaymond Dickey • AssociationHelpNow.com • [email protected] • www.AssociationHelpNow.comThis content does not constitute professional advice.
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Parking Garages & Concrete Nightmares: What Managers Must Catch Early
Parking garage and concrete problems rarely appear overnight — they usually start as small cracks, leaks, rust, water intrusion, worn sealants, or hidden deterioration that managers and boards may walk past for months or years. In this discussion, Scott Baryiewski of South Shore Construction and Tanner Oldenburger, PE, RS of Reserve Advisors explain the early warning signs managers should recognize, why water and salt are major enemies of concrete structures, how small maintenance issues can turn into major structural repairs, and why reserve planning is critical before a garage or façade project becomes overwhelming.------------------ YouTube: https://youtu.be/qmSQUJcW8YARegister for OnDemand 1h CEU Video - Parking Garages & Concrete Nightmares: What Managers Must Catch Early on Jun 9, 2026 12:00 AM EDT at:https://attendee.gotowebinar.com/register/8571071825597884254------------------The conversation also covers when to call an engineer versus a qualified contractor, why not every contractor is suited for structural concrete or garage restoration work, how staging and resident disruption affect major projects, and why boards should think carefully about maintenance plans, inspections, funding, and long-term reserve strategies.Scott Baryiewski • South Shore Construction, Inc. • [email protected] • www.ssc.contractorsTanner Oldenburger, PE, RS • Reserve Advisors, Inc. • [email protected] • www.reserveadvisors.comRaymond Dickey • AssociationHelpNow.com • [email protected] • www.AssociationHelpNow.comThis content does not constitute professional advice.
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HOA Know-It-Alls — The Psychology of How to Handle Them
HOA Know-It-Alls — The Psychology of How to Handle ThemEvery community has one… the “know-it-all.”They’ve read one statute, watched a video, or used AI—and now they’re ready to challenge management, the board, and even legal counsel. Sometimes they’re right. Often they’re not. Either way, they can disrupt meetings, create confusion, and undermine confidence in leadership.In this session, we break down the psychology behind know-it-alls and, more importantly, how managers and boards can handle them effectively—without escalating conflict or losing control of the room.=====================YouTube: https://youtu.be/BkKDswlMq9UOnDemand 1h CEU Video - HOA Know-It-Alls — The Psychology of How to Handle Them. Available to watch Jun 18, 2026 from 6:00 AM - 8:00 PM EDT.https://attendee.gotowebinar.com/register/1935027669822013526=====================What you’ll learn:• Why know-it-alls behave the way they do (and when they might actually be right)• How to respond without getting pulled into unproductive debates• Practical phrases and strategies to defuse tension• When to rely on professionals—and how to communicate that authority• How misinformation spreads in communities (especially online) and what to do about itPanel:Kristine Bates, CMCA, AMS, PCAM • Associa New York • [email protected] • https://www.associanewyork.comThomas Claus • Leisure Village Association • [email protected] Dickey • AssociationHelpNow.com • [email protected] • https://www.AssociationHelpNow.comTaylor Hayes, CMCA, AMS • CAMS • [email protected] • https://www.camsmgt.comHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice.#HOAManagement #CommunityAssociations #BoardLeadership #PropertyManagement #HOA #AssociationHelpNow
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Psychology of Groupthink in HOA Boards – When Governance Turns Dysfunctional
What do high-control groups and dysfunctional HOA boards have in common?——————YouTube: https://youtu.be/cIZ_4cK9VRY——————More than most people are comfortable admitting.In this provocative but practical session, we explore the psychology behind groupthink, dominant personalities, loyalty pressure, and information control—and how these dynamics quietly impact HOA and condo board decision-making.This is not about comparing community associations to cults.It’s about recognizing human behavior patterns that can undermine leadership, increase liability, and damage trust within your community.In this session, we break down:• How groupthink forms in volunteer HOA and condo boards• The danger of strong personalities dominating decisions• Why dissenting voices disappear—and why that creates risk• How misplaced loyalty can override fiduciary duty• The warning signs of an insular or isolated board• Practical strategies to restore transparency, balance, and accountabilityEvery board starts with good intentions.But without structure, awareness, and open dialogue, even well-meaning boards can drift into unhealthy governance patterns.If you are a community association manager or board member, this session will challenge your thinking—and give you practical tools to strengthen leadership and decision-making.It’s about behavior.PANELISTSRaymond Dickey • AssociationHelpNow® • www.AssociationHelpNow.comDavid Byrne, Esq. • Ansell Grimm & Aaron, PC • [email protected] • www.ansell.lawJennifer Hawk, CMCA, AMS • CAMS • [email protected] •www.camsmgt.comKristine Bates, CMCA, AMS, PCAM • Associa New York • [email protected]• www.associanewyork.com---Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice.---#HOA #CommunityAssociations #HOAManagement #BoardGovernance #PropertyManagement #CondoBoards #Groupthink #Leadership #AssociationManagement #HOABoard #CAM #CommunityManagement #BoardMembers #Governance #HOALeadership
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RFPs That Protect
Every major HOA or condo project starts long before the contract is signed.=======YouTube: https://youtu.be/PlAaUJTcYAU=======It starts with the RFP—and when it’s done wrong, everything that follows can fall apart.In this practical, real-world session, we break down how to structure a Request for Proposal that protects your association, creates true “apples-to-apples” bidding, and reduces the risk of disputes, delays, and budget overruns.From scope of work and vendor instructions to insurance requirements, timelines, and change orders, this discussion highlights what boards and managers must get right before the first bid ever comes in.You’ll also hear why poorly written RFPs lead to confusion, legal exposure, and project failure—and how a well-structured process can defend board decisions when they’re challenged.WHAT YOU’LL LEARN• Why the success of your project depends on the RFP• How to define scope of work to eliminate disputes• Why “apples-to-apples” bidding is critical• The real risk of relying on AI instead of professionals• How timelines, delays, and accountability should be structured• What causes change orders—and how to minimize them• Why insurance requirements can dramatically impact pricing• The role of engineers, attorneys, and insurance advisors• How to properly evaluate vendors and qualifications• Payment structures, retainage, and lien protection strategiesCEU INSTRUCTIONSTo qualify for CAMICB CEUs, please follow the on-screen instructions that appear during the video. These instructions will be displayed within the first 10 minutes of the program, so please watch carefully.To receive CEU credit, you must use the “Question” feature and respond to all three CAMICB checkpoints during the program. If these steps are not completed, we will not be able to submit your participation to CAMICB for credit.Please allow up to five days to receive your CEU confirmation.PANELRaymond Dickey • www.AssociationHelpNow.comGregg V. Gerelli • Gerelli Insurance Agency, Inc. • [email protected] • www.gerelli-insurance.comCory Kravit, Esq. • Kovitz Shifrin Nesbit • [email protected] • www.ksnlaw.comJohn LaGumina, Esq. • The LaGumina Law Firm, PLLC • www.laguminalaw.com • [email protected] Byrne, Esq. • Ansell Grimm & Aaron, PC • [email protected] • www.ansell.law]David Chesky, R.S., P.R.A. • Falcon Engineering • [email protected] • www.thefalcongroup.usWATCH / LISTENYouTube Channel: www.youtube.com/@AHNData/videosPodcast: https://www.buzzsprout.com/2565449Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice.#HOA #CondoAssociation #PropertyManagement #CommunityA
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AI May Already Be Creating Legal Risk for Your Association
AI is everywhere—but are community association boards and managers using it safely… or setting themselves up for lawsuits?==========================YouTube Video Full LiveStream: https://youtu.be/3iRk4l4n56s==========================In this eye-opening session, we break down the real-world risks of using AI in HOA and condo operations—from confidentiality breaches and copyright violations to insurance coverage gaps and potential negligence claims.You’ll hear how something as simple as copying text into AI or relying on it for decisions could expose your association to serious liability—including federal violations, data breaches, and even subpoenaed AI conversations.This is not theoretical. These issues are already happening.---What You’ll Learn• Why using AI for board decisions can backfire in court• The hidden danger of entering confidential HOA data into AI tools• Open AI vs. closed AI—what boards MUST understand• How AI can accidentally copy copyrighted material (and cost you The • Why “we didn’t know” won’t protect your association• Insurance gaps: when coverage may NOT apply• Why board members still carry full fiduciary responsibility• How AI use by vendors and managers can expose your association• Simple policies every board should adopt immediately---PanelRaymond DickeyAssociationHelpNow®www.AssociationHelpNow.comDawn Becker-Durnin, [email protected] P. Hager, Esq.Kyberia [email protected] Should Watch:HOA Managers, Condo Boards, Community Association Leaders, Insurance Professionals, and Anyone Using AI in Association Operations---Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice.---#HOA #CondoBoards #PropertyManagement #AI #ArtificialIntelligence #HOAmanagement #CommunityAssociations #CyberRisk #HOAlegal #Insurance #DataPrivacy #BoardMembers #RiskManagement
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Reserve Funding Isn’t a Math Problem
This interview was based on a recent LinkedIn post from Michelle Baldry.YouTube: https://youtu.be/IzXnCaRJ2swIn her post, Michelle Baldry, PE, PRA, RS as Chair of the Foundation for Community Association Research’s Best Practices shared insights from a national reserve funding survey that highlighted a key issue: many communities aren’t underfunded due to lack of awareness, but because of how difficult these decisions are to communicate and implement.LinkedIn Post: https://www.linkedin.com/posts/michelle-baldry_communityassociationresearch-hoa-reservefunding-activity-7432468970303033344-2kjj?utm_source=share&utm_medium=member_desktop&rcm=ACoAAA1xftoBOhA1qKbJiwA4J9SAeYTF83ToYHIReserve funding isn’t a math problem, it’s a communication problem.In this discussion, we cover:- Why 64% say communication—not numbers—is the biggest challenge- What boards understand… but struggle to convey to homeowners- How reserve studies are evolving into risk mitigation tools- Why lenders and insurers are paying closer attention- Common mistakes when presenting funding planPractical ways to position reserves so communities understand the long-term impactThis video builds directly on Michelle’s original post, turning the data into real-world application for community association managers and board members.If you’ve ever had pushback on reserves, delayed funding decisions, or struggled to explain the “why” behind increases, this is worth your time.Panel:Michelle Baldry, PE, PRA, RS • Reserve Advisors, Inc. • [email protected] • www.reserveadvisors.comRaymond Dickey • www.AssociationHelpNow.comHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice.#HOA #CondoLiving #CommunityAssociations #PropertyManagement #ReserveStudies #HOABoard #FinancialPlanning #RiskManagement #SpecialAssessments #AssociationManagement
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HOA Collections Explained
HOA Collections Explained: Liens, Foreclosure, Bankruptcy, Payment Plans, and Board Collection MistakesCollecting assessments is not optional for HOA and condo boards. It is a fiduciary duty. But when collections are handled inconsistently or without the right legal process, associations can create serious risk, including selective enforcement claims, Fair Debt Collection issues, confidentiality problems, board liability, and unnecessary conflict with owners.———————————-YouTube: https://youtu.be/f_DW7pZFeMsCAMICB CEU Video: Please register for CEU Video - “HOA Collections Explained” Apr 16, 2026 (1 hour video available all day) at:https://attendee.gotowebinar.com/register/5185089483040991574———————————-In this practical livestream recording, our panel breaks down how community association collections really work, including liens, foreclosure timelines, notice requirements, bankruptcy complications, payment plans, late fees, money judgments, suspension of privileges, and why written collection policies matter. The discussion also covers what boards can and cannot do when owners claim hardship, whether compassion can affect enforcement, how different states handle collection timelines, and why delaying action can damage association cash flow and increase legal exposure.This is a must-watch for HOA board members, condo board members, community association managers, and anyone responsible for protecting association finances while enforcing governing documents fairly and consistently.This recording is especially helpful if your community is dealing with delinquent owners, inconsistent enforcement, unpaid assessments, bankruptcy filings, lien questions, foreclosure concerns, or board uncertainty about how aggressive collections should be.PANEL:Raymond Dickey • www.AssociationHelpNow.comDawn Becker-Durnin, CIRMS • Acrisure • [email protected] • www.acrisure.comDavid Byrne, Esq. • Ansell Grimm & Aaron, PC • [email protected] • www.ansell.lawAdam Clarkson, Esq. • Clarkson McAlonis & O’Connor, P.C. • [email protected] • www.cmolawpc.comElliot M. Engstrom, Esq. • Sellers, Ayers, Dortch & Lyons, P.A • [email protected] • www.SellersAyers.comGregg V. Gerelli • Gerelli Insurance Agency, Inc. • [email protected] • www.gerelli-insurance.comCory Kravit, Esq. • Kovitz Shifrin Nesbit • [email protected] • www.ksnlaw.comJohn LaGumina, Esq. • The LaGumina Law Firm, PLLC • [email protected] • www.laguminalaw.comHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice.#HOACollections #HOALiens #HOAForeclosure #HOABankruptcy #AssociationCollections #CondoCollections #CommunityAssociationLaw #HOABoard #CondoBoard #PropertyManagement #CommunityAssociationManager #HOAAssessments #DelinquentOwners #CollectionsPolicy #HOALaw #CondoLaw #AssociationHelpNow #BoardGovernance
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Massive Boulder Blast Update + Can Managers Be Friends With Board Members?
A routine HOA-area blast turned into a nightmare when huge rocks crashed into homes, damaged association property, and triggered major insurance, liability, and communication issues. In this livestream recording, we revisit one of the most shocking HOA incidents discussed this year and break down what happened next. Were the homes repaired? Who ended up paying? What did the insurance process look like? What should managers and boards do immediately after a disaster like this?YouTube Video: https://youtu.be/gaXNpfrbMrwCEU Video - HOA Blast Update + Are Manager–Board Friendships Appropriate On-Demand 1 hour, All Day Apr 21, 2026 12:00 AM EDT at: https://attendee.gotowebinar.com/register/9164698152445669470This session is especially valuable for HOA managers, condo board members, community association leaders, and anyone involved in property management, insurance claims, reserve planning, risk management, or resident communication. The discussion covers real-world lessons about emergency response, documentation, inspections, owner updates, disaster planning, and how fast a community can spiral if the wrong steps are taken.Then the conversation shifts to a topic that hits just as close to home: can HOA managers and board members really be friends? It sounds harmless, but this is where perception, favoritism concerns, gossip, influence, and professional boundaries can create serious problems. The panel discusses when being friendly crosses the line, how optics affect trust, and what managers should do to protect their neutrality and credibility.This recording includes practical takeaways on: HOA disaster response, community association insurance issues, claims handling, liability questions, owner communication, manager professionalism, board relationships, and avoiding hidden conflicts.Original livestream referenced in this program: “HOA Hit by 45 pound Rocks!”https://youtu.be/9UCgBm4-EsUHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.PANEL:Raymond Dickey • www.AssociationHelpNow.comDawn Becker-Durnin, CIRMS • Acrisure • [email protected] • www.HOAInsuranceSC.comChris Petrik, CMCA, AMS, PCAM • Bulle Rock Community Association • [email protected] • www.bullerockcommunity.comChris Lozier, CMCA • Ponderosa Management LLC • [email protected] content does not constitute professional advice.#HOA #HOADisaster #PropertyManagement #CommunityAssociation #CondoAssociation #HOAInsurance #InsuranceClaims #RiskManagement #DisasterPlanning #HOABoard #AssociationManagement #CommunityManagers #ProfessionalBoundaries #BoardMemberRelations #CondoManagement #HOALiability
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HOA Special Assessments: How to Communicate Them, Avoid Legal Mistakes, and Decide If Borrowing Is Smarter
Special assessments are one of the toughest challenges HOA and condo boards face. In this practical livestream, our panel explains how boards and managers can communicate a special assessment without creating panic, avoid procedural mistakes that often lead to disputes or litigation, and evaluate when borrowing may be the better option. The discussion covers owner communication, governing document requirements, voting procedures, collections, insurance considerations, reserve shortfalls, and lender perspectives.———————————————CAMICB CEU Video: Please register for CEU Video - Special Assessments - Sell, Structure or Borrow It on Apr 14, 2026 (1 hour video available all day) at:https://attendee.gotowebinar.com/register/1613926293455377495———————————————If you are a community association manager, board member, or industry professional looking for guidance on special assessments, association loans, reserve funding, owner communication, fiduciary duty, or major repair funding decisions, this recording provides practical insight on structuring the process, explaining the need, and reducing owner backlash.PANEL:Raymond Dickey • www.AssociationHelpNow.comDeborah Gerelli, CIRMS • Gerelli Insurance Agency, Inc. • [email protected] • www.gerelli-insurance.comDawn Becker-Durnin, CIRMS • Acrisure • [email protected] • www.HOAInsuranceSC.comJohn LaGumina, Esq. • The LaGumina Law Firm, PLLC • [email protected] • www.laguminalaw.comCynthia Jones, Esq. • Sellers, Ayers, Dortch & Lyons, P.A. • [email protected] • www.sellersayers.comThomas Engblom, PhD., PCAM • First Citizens Bank • [email protected] • www.bankers.firstcitizens.comSean A. O’Connor, Esq., CCAL • Clarkson McAlonis & O’Connor, P.C. • [email protected] • www.cmolawpc.comDavid Byrne, Esq. • Ansell Grimm & Aaron, PC • [email protected] • www.ansell.lawCory Kravit, Esq. • Kovitz Shifrin Nesbit • [email protected] • www.ksnlaw.comHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice.#HOA #CondoAssociation #SpecialAssessments #HOABoard #PropertyManagement #CommunityAssociations #ReserveFunding #AssociationLoans #CondoBoard #HOALaw #CondoLaw #BoardGovernance #CapitalProjects #HOAManagers #FiduciaryDuty
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AI in HOAs - Powerful Tool or Legal Time Bomb
Artificial Intelligence is already inside community associations.---- This video is not eligible for CEUs ----YouTube Video: https://youtu.be/kRXYzKmLAzcManagers are using it to draft emails.Boards are asking it to interpret bylaws.Vendors are embedding it into software platforms.But here’s the real question: Are we using AI wisely — or creating new liability without realizing it?In this livestream, we’re breaking it down the way we always do — practical, real-world, and balanced.We’ll look at:• How AI can dramatically improve communication and efficiency• What happens when boards rely on AI instead of legal counsel• Confidentiality concerns most managers haven’t thought about• Deepfake fraud, cyber exposure, and vendor accountability• Whether associations should adopt an AI usage policyThis is not a tech lecture.It’s a candid discussion about how managers and boards can use AI responsibly — without turning a helpful tool into a silent liability.If you manage or serve on a board, this conversation is no longer optional.AI is here. The question is whether we understand the risks that come with it.Panel:Cameron Leyh, CMCA, AMS • Ravenel Associates, Inc. • [email protected] Dickey • AssociationHelpNow.comDawn Becker-Durnin, CIRMS • Acrisure • [email protected] • www.HOAInsuranceSC.comValerie Garcia Giovanoli, Esq. • McCabe, Trotter & Beverly, P.C. • [email protected] • www.mccabetrotter.comContent does not represent professional advice.
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HOA Bankruptcy Explained: Can a Condo Association Really Go Broke?
When an HOA or condominium association files bankruptcy, what actually happens?Can the board just declare bankruptcy?Do owners become personally responsible?Can a creditor force an HOA into bankruptcy?And can a bankruptcy judge really wipe out amenities—or even force massive special assessments?YouTube Video: https://youtu.be/q8w39unoeqICEU Version: https://attendee.gotowebinar.com/register/8461299881746255964In this special AssociationHelpNow® session, Ray Dickey sits down with Florida attorney Cory Kravit and tri-state attorney Dave Byrne to break down a real Florida case involving a recreational condominium that filed Chapter 11 bankruptcy.This video covers:✔ Why an association would file Chapter 11✔ What happens when sub-associations stop paying✔ How bankruptcy affects owners, assessments & foreclosures✔ Whether amenities or common property can be sold✔ Why older buildings and deferred maintenance matter✔ How terminations vs. bankruptcy differ✔ The role of board fiduciary duty during financial crises✔ Whether a bankruptcy court can override governing documents✔ What creditors can and cannot do✔ The “toll booth” hypothetical that had everyone laughingThis is one of the most detailed, real-world bankruptcy discussions ever streamed for HOAs and condos. If you are a manager, board member, homeowner, or attorney, this deep dive will dramatically improve your understanding of how bankruptcy truly works in community associations.PANEL (Recorded Feb., 23, 2026):Raymond Dickey • www.AssociationHelpNow.comDavid Byrne, Esq. • Ansell Grimm & Aaron, PC • [email protected] • www.ansell.lawCory Kravit, Esq. • Kovitz Shifrin Nesbit • [email protected] • www.ksnlaw.comHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice.
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Protecting Managers & Boards from Abusive Residents
Have you ever had an owner say something like, “Send me another violation and you’ll regret it. I’ll come down there and deal with you myself”… and you’re left wondering: Is that just rude—or is it a threat?YOUTUBE: https://youtu.be/qpV8O5807doIn this conversation, I sit down with community association attorneys, an insurance professional, an engineer, and an on-site manager of a 1,100+ home community to tackle one uncomfortable question: where is the line between angry, abusive, and legally actionable?We talk about:Real-world examplesWhether police, HR, and legal counsel can actually helpHow boards can truly have their manager’s backCodes of conduct, behavior policies, fines, and enforcement limitsDe-escalation phrases and tactics managers actually rely onIf you’re tired of boards and managers being “punched bags” for bad behavior—but you also don’t want to silence legitimate complaints—this video will give you language, perspective, and options you can use in your community.Panel:Raymond Dickey • www.AssociationHelpNow.comDavid Byrne, Esq. • Ansell Grimm & Aaron, PC • [email protected] • www.ansell.lawJohn LaGumina, Esq. • The LaGumina Law Firm, PLLC • [email protected] • www.laguminalaw.comJustin Bailey, CMCA • AAM, LLC • [email protected] V. Gerelli • Gerelli Insurance Agency, Inc. • [email protected] • www.gerelli-insurance.comDavid Chesky, R.S., P.R.A. • Falcon Engineering • [email protected] • www.thefalcongroup.usHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice.#HOAManagement #CommunityAssociations #PropertyManagement #BoardMembers #CommunityManagers #HOALaw
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Maintenance Mysteries - The Hidden Failures That Blow HOA Budgets
Why do some building failures look simple… until you open a wall and find ten new problems? In this livestream, I sit down with an industry leader who specializes in the toughest maintenance and construction diagnostics facing HOAs today — from mysterious deck failures and chronic mold issues to roof leaks, flashing mistakes, siding cracks, skylight problems, paint delamination, incompatible coatings, gutter undersizing, and full-replacement decisions that catch boards off guard.We’ll break down the real causes behind the failures that cost communities the most — and the questions managers and boards should ask before approving work. If you’ve ever wondered why bids can vary by 40%, why leaks return after repairs, or why moisture keeps finding its way in, this session is your chance to get clear answers.YouTube Video: https://youtu.be/XaPSyNwFbwwRaymond Dickey • AssociationHelpNow.comTodd Vignola • Add Ventures, Inc. • [email protected] • www.addventuresinc.comDavid Chesky, R.S., P.R.A. • Falcon Engineering • [email protected] • www.thefalcongroup.usHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.Does not constitute professional advice.
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CEU VERSION: Dock and Dam Liabilities That Blow Budgets
Docks and dams age quietly, fail suddenly, and can become budget-wrecking fast if boards and managers don’t spot the warning signs early. This livestream breaks down the hidden structural, environmental, regulatory, and ownership liabilities that too often slip past reserve schedules and end up blindsiding associations with massive surprise costs. We’ll cover what should be evaluated, how to anticipate lifecycle and safety risks, and the questions every manager should be asking long before small deficiencies turn into emergencies.———————— Podcast CAMICB CEU Instructions: Log into: https://lp.constantcontactpages.com/ev/reg/gebjdyfLog into the above before you start listening to the podcast. Simply follow the instructions. It's not complicated.———————— PANEL:Raymond Dickey • AssociationHelpNow.comDawn Becker-Durnin, CIRMS • Acrisure • [email protected] • www.HOAInsuranceSC.comMatt Kuisle, PE, PRA, RS • Reserve Advisors, Inc. • [email protected] • www.reserveadvisors.comTulin Fuselier, PE • Weston & Sampson • [email protected] • www.westonandsampson.comAssociationHelpNow® | Practical insights for managers and boards who live this every day.Does not constitute professional advice.
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17
Dock & Dam Liabilities That Blow Budgets
Docks and dams age quietly, fail suddenly, and can become budget-wrecking fast if boards and managers don’t spot the warning signs early. This livestream breaks down the hidden structural, environmental, regulatory, and ownership liabilities that too often slip past reserve schedules and end up blindsiding associations with massive surprise costs. We’ll cover what should be evaluated, how to anticipate lifecycle and safety risks, and the questions every manager should be asking long before small deficiencies turn into emergencies.Find the video at: https://www.youtube.com/@AHNData/videosPANEL:Raymond Dickey • AssociationHelpNow.comDawn Becker-Durnin, CIRMS • Acrisure • [email protected] • www.HOAInsuranceSC.comMatt Kuisle, PE, PRA, RS • Reserve Advisors, Inc. • [email protected] • www.reserveadvisors.comTulin Fuselier, PE • Weston & Sampson • [email protected] • www.westonandsampson.comAssociationHelpNow® | Practical insights for managers and boards who live this every day.Does not constitute professional advice.
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16
Hazard Zones - Retaining Walls as a Reserve Problem
Retaining walls rarely get attention until the ground shifts—literally. This session breaks down why these structures are among the most overlooked high-risk components in community associations and how hidden drainage issues, soil movement, and aging construction quietly set the stage for major failures.YouTube: https://youtu.be/gucX_IWBz6sWe’ll cover what managers and boards must document, how to spot early warning signs, and why retaining walls are a financial hazard zone when reserves underestimate real replacement costs. Most importantly, we’ll look at the safety side—because these aren’t just dollars and line items. A wall failure can injure someone. Knowing what to look for, and acting early, can prevent the kind of event every board hopes never happens.Raymond Dickey • AssociationHelpNow.comAlan Ebert, PE, PRA, RS • Reserve Advisors, Inc. • [email protected] • www.reserveadvisors.comDawn Becker-Durnin, CIRMS • Acrisure • [email protected] • www.HOAInsuranceSC.comJohn LaGumina, Esq. • The LaGumina Law Firm, PLLC • [email protected] • www.laguminalaw.comAssociationHelpNow® | Practical insights for managers and boards who live this every day.Livestream does not constitute professional advice.
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15
Luxury High-Rise Jeffrey Ulm Interview: Miami’s Ultra-Exclusive World
Luxury High-Rise Jeffrey Ulm Interview: Inside Miami’s Ultra-Exclusive WorldThe Brickell/Miami high-rise world is nothing like typical association management. From cold plunges and cigar lounges to 100-story towers, Bentley deliveries, branded buildings, concierge-level expectations, and the intense hospitality standard required to succeed… this interview with Jeffrey Ulm, CMCA, AMS, PCAM gives managers and board members a rare inside look at one of the most demanding management environments in the country.Walk with us through what “perfection” really means when residents fly in for only two weeks a year and expect every elevator, amenity, and service touchpoint to operate flawlessly. You’ll hear about hidden pressures, surprising perks, how luxury managers develop their careers, and why these buildings are actually some of the most rewarding places to work, if you’re built for it.Video: https://youtu.be/IJu9_K5mPHYRaymond Dickey • AssociationHelpNow https://www.linkedin.com/in/raymondjdickeyJeffrey Ulm, CMCA, AMS, PCAM • FirstService Residential • [email protected] • www.fsresidential.comHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice and may have been edited.#HOAManagement #CommunityAssociations #PropertyManagement
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14
High Rise Luxury Management: What Happens Behind the Front Desk
Inside Luxury High Rise Management: What Happens Behind the Front DeskCurious what separates a high end building from a true luxury high rise?This conversation gives you a rare look at the service culture, resident expectations, and leadership mindset required to operate in one of the most demanding segments of the community association world.You will hear what happens when highly successful residents expect immediate service, how managers build a high performance staff culture, and the surprising myths that many managers and board members still believe about luxury properties.If you want to understand how elite communities actually function behind the scenes, this is the video to watch.Raymond Dickey • AssociationHelpNowhttps://www.linkedin.com/in/raymondjdickeyJeffrey Ulm, CMCA, AMS, PCAM • FirstService Residential • [email protected] • www.fsresidential.comFind More Videos: https://www.youtube.com/@AHNData/videosFind Great PodCasts: https://www.buzzsprout.com/2565449Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice and may have been edited.#HOAManagement #CommunityAssociations #PropertyManagement
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13
Rule Enforcement Traps Boards Don’t See Coming
Rule Enforcement Traps Boards Don’t See ComingOne “simple” rule violation can turn into a privacy complaint, discrimination claim, or a D&O headache fast—especially when boards and managers improvise enforcement.YOUTUBE: https://youtu.be/MQ_5Knn2mBYIn this session, we pressure-test real-world scenarios that feel straightforward… until they aren’t:“Reasonable accommodation” requests (and what you can ask for without creating a bigger problem)Warnings, hearings, and consistency (what courts and owners often expect—even when your docs don’t spell it out)Documentation landmines: photos, interviews, surveillance, interior visibility, and “how far is too far?”The unspoken risk: rule enforcement that accidentally becomes about something elsePlus: “You’re the Judge” cases that split even attorneys (signs, door decor, locker rooms, and more)If you’ve ever thought, “Why is this getting so messy?”—this is why.David Byrne, Esq. • Ansell Grimm & Aaron, PC • [email protected] • www.ansell.lawRaymond Dickey • AssociationHelpNow.comGregg V. Gerelli • Gerelli Insurance Agency, Inc. • [email protected] • www.gerelli-insurance.comCory Kravit, Esq. • Kovitz Shifrin Nesbit • [email protected] • www.ksnlaw.comJohn LaGumina, Esq. • The LaGumina Law Firm, PLLC • [email protected] • www.laguminalaw.comCynthia Jones, Esq. • Sellers, Ayers, Dortch & Lyons, P.A. • [email protected] • www.sellersayers.comO’Neil McCoy, MRED, CLCS • McGriff • [email protected] • www.mcgriffinsurance.comMatthew W. Heron, Esq. • • Hirzel Law, PLC • [email protected] • www.hirzellaw.comHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.#HOAManagement #CommunityAssociations #PropertyManagement
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12
The Four Corners Rule
The Four Corners Rule: If It’s Not Written, It Doesn’t ExistWhen disputes arise, it’s not about what someone meant, it’s about what’s written. The Four Corners Rule is the legal principle that says only the words within a document itself count. For boards, managers, and even vendors, that can mean the difference between being protected or being exposed.YouTube: https://youtu.be/bj6katQnIgcJohn LaGumina, Esq. / David Byrne, Esq. / Deborah Gerelli, CIRMS / Michael Pereira, Esq. / Cory Kravit, Esq. / Christian Saville, Esq. Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice.
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11
HOA Manager Roundtable - It’s Water
Community Manager Roundtable – Live Interactive Livestream - Plus: Let's Talk Bodies - of Water. Kristine Bates, CMCA, AMS, PCAM / Thomas Claus / Nichole M. Haddock, CISR / David Byrne, Esq. Hosted by AssociationHelpNow®.#HOAManagement #CommunityAssociations #PropertyManagement
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10
Hidden Reserve Infrastructure Risks Communities Miss
Communities miss the danger they can’t see. Hidden infrastructure failures hit fast — and hit hard. Get ahead before the liability lands on you.In-depth and basic reserve questions answered.Michelle Baldry, PE, PRA, RS • Reserve Advisors, Inc. • [email protected] • www.reserveadvisors.comRaymond Dickey • AssociationHelpNow.comHosted by AssociationHelpNow®#HOAManagement #CommunityAssociations #PropertyManagement
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9
The Quiet Work Habits That Prevent Manager Burnout
Protect your mornings, defend your focus, and cut hidden burnout risks fast. Small habits beat stress when the pressure hits.Taylor Hayes, CMCA, AMS • CAMSRaymond Dickey — Hosted by AssociationHelpNow®HOAManagement #CommunityAssociations #PropertyManagement
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8
Annual Association Checklist Most Boards Quietly Miss
Most HOA problems aren’t sudden—they’re missed reviews: coverage, finances, contracts, enforcement.Run this annual checklist and catch the quiet risk before it becomes liability.Raymond Dickey / Christian Saville, Esq. / John LaGumina, Esq. / Jeremy Fernando, Esq. / Gregg Gerelli / Dawn Becker-Durin, CIRMS / David Byrne, Esq. / Cory Kravit, Esq. / Elliot M. EngstromHosted by AssociationHelpNow®.#HOAManagement #CommunityAssociations #PropertyManagement
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7
The Normalized Manager Risk That No One Talks About
Managers face pressure and behavior that would never be tolerated in any other industry. Here’s the overlooked liability that can escalate fast — and how to respond. Strong, practical insights managers can use today.Taylor Hayes, CMCA, AMS • CAMS Raymond Dickey— Hosted by AssociationHelpNow® #HOAManagement #CommunityAssociations #PropertyManagement
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6
Construction Defect Traps That Can Cost Your HOAs
Construction Defect Traps That Can Cost Your HOAsBefore You “Handle It Yourself”!Video also available on YouTube: https://youtu.be/fnM8g2zEUkQConstruction defects aren’t just “a few broken roof tiles.” In this Florida + South Carolina-focused conversation, two community association attorneys get practical about what really happens after turnover— when something isn’t working, water starts showing up where it shouldn’t, or a “quick fix” turns into a community-wide financial problem.Panel:Adam Clarkson, Esq. • Clarkson McAlonis & O’Connor, P.C. • [email protected] • www.cmolawpc.comCory Kravit, Esq. • Kovitz Shifrin Nesbit • [email protected] • www.ksnlaw.comWe dig into the stuff boards and managers don’t always hear until it’s too late:What “construction defect” usually means vs. what it actually means (and what isn’t a defect)The real difference between defects, warranties, and maintenance failures—and why it mattersThe clock issues boards underestimate: statute of limitations vs. statute of repose (and how delays happen)Florida’s Chapter 558 process (the “558 letter”) and why notice/detail mattersA major board mistake: bringing in experts without legal counsel—and how privilege/work product changes everythingWhat to collect at turnover: plans, manuals, warranties, system docs—because “it disappears”When inspections are truly necessary (especially for larger buildings), what it can cost, and why skipping it can become a fiduciary problemHow attorneys get paid in defect cases: hourly, contingency, and hybrid—and what boards should considerRed flags: releases/waivers, “don’t call a lawyer” advice, and the slow-motion way claims get lostIf you’re a manager or board member trying to protect your community’s future budget (and avoid being the board everyone blames later), this is the “deep dive” version—not the quick article summary.If you are need for CEUs go to: Register for Construction Defect Traps That Can Cost Your HOAs - FL - SC on Jan 14, 2026 9:00 AM EST at:https://attendee.gotowebinar.com/register/821766647061919838Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. This content does not constitute professional advice and may have been edited.#HOA #Condominium #CommunityAssociations #ConstructionDefects #HOALaw #CondoAssociation #PropertyManagement #BoardOfDirectors
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5
Your HOA Is a Prime Cyber Target and How They Will Trick You
Community associations are sitting on something criminals want—money, data, and access—and many boards don’t realize how exposed they really are until after a loss occurs.In this episode, Raymond Dickey of AssociationHelpNow® is joined by insurance expert Dawn Becker-Durnin, CIRMS for a candid, real-world discussion about how cybercrime actually impacts HOAs and condominium associations. From phishing and fake vendors to altered electronic checks and wire transfer fraud, they break down how schemes work, why they’re so effective, and why even experienced managers and board members can fall victim at exactly the wrong moment.The conversation also explores a critical misconception: the belief that management companies, banks, or standard insurance policies will automatically cover these losses. As Dawn explains, coverage often depends on how the crime occurred—and in many cases, associations discover too late that they’re on their own.If you’re a board member, manager, or industry professional trying to understand today’s cyber risks, insurance gaps, and fiduciary responsibilities without legal jargon or fear-based sales tactics, this episode delivers the clarity most associations don’t get until after a crisis.Raymond Dickey • AssociationHelpNow.comDawn Becker-Durnin, CIRMS • Acrisure • [email protected] by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice and may have been edited.
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4
New Jersey HOA Bills - $2000 Fines, Shady Boards, HOA Hydrants and More
We sit down with Assemblyman Donald A. Guardian and HOA attorney David Byrne, Esq. to break down a stack of HOA/condo bills that sound simple… until you realize what they could mean for real communities.You’ll hear:The bill that could let the state fine associations $2,000 per instance for late meeting minutes (and why enforcement is the real concern)A developer-control proposal that sounds like a no-brainer—so why might it stall anyway?The bill that would shift condo insurance deductible costs from affected units to everyone (and why that could backfire)Why HOA road fire hydrants are even a debate (and who might fight that change)A push for property management licensing—and the “details problem” that decides whether it helps or hurtsThe “board shady business” bill: conflicts, relatives, disclosures… and what the law actually allows todayPlus: a brutally honest (and funny) reality check on how bills really move in Trenton—spoiler: it’s not like the movies.Drop your state in the comments—if you’re dealing with similar issues, I’ll queue up more of these “what this REALLY means” breakdowns.Panel:Donald A. Guardian • [email protected] Byrne, Esq. • Ansell Grimm & Aaron, PC • [email protected] Dickey • AssociationHelpNow.comNeed CAMICB CEUs? Go to AssociationHelpNow.com to watch the video on our CEU link.Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.
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3
The Construction Defect “Triangle” - Win Or Waste A Fortune
Most boards don’t ignore construction defects on purpose. They ignore them because they don’t realize the window is closing while they’re “working it out” with the developer.In this recorded conversation, two seasoned community association attorneys break down what actually happens when a defect shows up: why “it passed inspection” doesn’t protect you, why waiting can quietly erase claims, and why the smartest move is often not arguing about blame—it’s locking in the right experts early so you don’t get cornered later.You’ll also hear the framework that cuts through the noise (the three-legged stool / “Golden Triangle” that determines whether a case is worth pursuing), plus the uncomfortable truth about insurance, collectability, and why fraud claims can backfire even when everyone knows something was left out.If you’re a manager or board member dealing with leaks, cracks, drainage issues, mysterious water intrusion, or a “fix” that keeps coming back—this is the conversation you want to hear before the next meeting.Panel:Raymond Dickey • AssociationHelpNow.comDavid Byrne, Esq. • Ansell Grimm & Aaron, PC • [email protected] • www.ansell.lawKevin Hirzel, Esq. • Hirzel Law, PLC • [email protected] • www.hirzellaw.comNeed CEUs? Go to www.AssociationHelpNow.comHosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice and may have been edited.#HOA #Condo #CommunityAssociations #PropertyManagement #HOABoard #CondoBoard #BoardMembers #CommunityManager #ConstructionDefects #Turnover #DeveloperTurnover #FiduciaryDuty #RiskManagement #InsuranceClaims #EngineeringReport #ReserveStudy #BuildingEnvelope #WaterIntrusion #BuildingMaintenance #AssociationHelpNow
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ABOUT THIS SHOW
AssociationHelpNow® delivers practical, real-world conversations for community association managers and board members who live this work every day. Each episode features candid discussions, expert interviews, and timely insights covering legal, insurance, operational, leadership, and communication challenges facing HOAs and condominiums. From livestream highlights to workshop takeaways, the show bridges the gap between theory and practice—helping listeners make smarter, more confident decisions in complex environments.Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice and may have been edited.
HOSTED BY
Raymond Dickey
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