Should You Start With Long-Term or Short-Term Rentals?

If you're a teacher or busy professional wondering whether to begin your real estate journey with long-term rentals (LTRs) or short-term rentals (STRs) like Airbnb, this episode breaks down the decision clearly and practically.Host Michel Chavannes shares the key advantages and challenges of each strategy and explains how your schedule, budget, lifestyle, and risk tolerance should guide your investment choice. Instead of chasing trends, this episode helps you choose the strategy that actually fits your life today.What You’ll Learn in This EpisodeThe difference between long-term vs short-term rentalsWhy investment strategy is a lifestyle decisionPros and cons of each rental approachWhich option works best for busy educatorsHow to evaluate your time availability before investingQuestions to ask yourself before choosing your first propertyWhy your first strategy doesn’t have to be permanentLong-Term Rentals (LTR) — Pros✔ Predictable monthly income✔ Lower time commitment✔ Easier financing approval from banks✔ Beginner-friendly structure✔ Ideal alongside a full-time teaching jobChallenges⚠ Slower monthly cash flow growth⚠ Tenant laws can complicate exits⚠ Limited flexibility with rent changes and property useBest for: Investors who want a stable, low-maintenance entry pointShort-Term Rentals (STR) — Pros✔ Higher income potential in strong markets✔ Flexible pricing during events and peak seasons✔ Personal-use availability when needed✔ Creative opportunity through design and hospitalityChallenges⚠ Requires active management systems⚠ Must follow local STR regulations⚠ Higher upfront furnishing costs⚠ Seasonal income fluctuationsBest for: Investors comfortable with hands-on involvement and variabilityQuestions to Help You DecideAsk yourself:How much time can I realistically manage each week?Do I prefer stability or upside potential?Is my local market STR-friendly?Does this strategy match my current lifestyle?There’s no universal right answer. Only the right answer for this stage of your life.Real Example from the HostMichel began with a long-term rental duplex, living in one unit and renting the other. Later, after gaining experience and more flexibility, he explored short-term rentals for their creativity and tax advantages.Key TakeawayYou don’t need to commit forever. Start with the strategy that fits your schedule and confidence level today, then evolve as your capacity grows.Connect With the CommunityJoin the conversation:DM @ChalkboardsToCashFlow on InstagramShare whether you're Team LTR or Team STRJoin the free Chalkboards to Cash Flow Facebook groupIf This Episode Helped YouFollow the showLeave a reviewShare with a fellow educator or new investorRemember: You don’t need to be rich to start. You just need to start. 💡