Landlord DIY vs Hire Out: What to Handle Yourself episode artwork

EPISODE · Aug 29, 2026 · 22 MIN

Landlord DIY vs Hire Out: What to Handle Yourself

from Your Landlord Resource Podcast · host Stacie Casella & Kevin Kilroy

Send us Fan MailEvery landlord has to make the decision to DIY a task or hire it out. Something breaks, you have got your phone in one hand, ready to call the tech, and a YouTube tutorial in the other to see if you can manage the task yourself…and you are doing the math.The idea for this episode came from a listener who asked what he should be doing himself and what he should be paying someone else to do. Honestly? It’s a pretty vague question. That is exactly why it is a good one, because it is not just one question! It’s a maintenance question, a legal question, a bookkeeping question, and a do I even want to be a property manager question.Kevin opens the episode with the four-question filter we run before we touch anything. It takes about ten seconds, and question four is the one that surprises people, because it pushes back the other way.Then I walk through the five things we will not hand off no matter how buried we get, including the one most landlords give away without realizing what they gave up. Kevin follows with the list where the best decision is to just spend the money.Plus, the middle lane almost nobody knows exists, why our attorney's hourly rate makes us better DIYers, and the contractor who might be the best business decision we have ever made.Hit play. You will walk away with a filter you can use on the very next thing that breaks.What You'll Learn in This Episode●     The four-question filter we run before deciding to DIY or hire out●     Why "can I learn this on YouTube" was never the right question●     The one rule about permits that ends the debate instantly●     Five jobs we keep in-house no matter how busy we get●     The work we always pay for, and the insurance risk if you don't●     What changed in 2025 that gives your tenant twice as long to respond●     Why holding property in an LLC removes an option you may think you have●     The à la carte management setup most landlords never think to ask forEpisodes & Resources MentionedEpisode 3: Spring Maintenance ChecklistEpisode 109: Fall Maintenance RecapEpisode 14: Building Your Maintenance Team, Pt 1Episode 15: Your Office Operations & Business Team, Pt 2Episode 16: Is Holding Your Rental Property in an LLC Right for You?Episodes 39–40: 50+ Must Ask Questions When Hiring a Property ManagerEpisode 88: Should Landlords Get Their Real Estate License?Episode 96: Tips from Our ContractorEpisode 137: Emergency Maintenance vs Routine RepairsDoorLoop: Landlord software for larger portfoliosTurboTenant: Landlord software for newer landlordsEZ Landlord Forms: State-specific lease and notice formsAffiliate Disclosure: This episode may contain affiliate links. Your Landlord Resource may earn a commission if you purchase through our links, at no additional cost to you. We only recommend products and services we believe in. These small commissions are to benefit our business so thank you for your support.Legal Disclaimer: Nothing in this episode constitutes personalized legal or financial advice. Always consult a licensed real estate attorney or CPA for guidance specific to your state, city, and situation.Connect with Us: 🌎 Visit our website 📧 Subscribe to our newsletter.👆 FREE Landlord Forms and Doc’s🤳Text Us: 650-489-4447📩Email us at: [email protected], [email protected] ➡️ Give us a review: Apple or on Spotify or YouTube ✔️Course Waitlist📱 Instagram, Facebook, &  Private Facebook group 

Episode metadata supplied by the publisher feed · Published Aug 29, 2026

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Send us Fan Mail Every landlord has to make the decision to DIY a task or hire it out. Something breaks, you have got your phone in one hand, ready to call the tech, and a YouTube tutorial in the other to see if you can manage the task yourself…and you are doing the math. The idea for this episode came from a listener who asked what he should be doing himself and what he should be paying someone else to do. Honestly? It’s a pretty vague question. That is exactly why it is a good one, because ...

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