Starting with wholesaling and planning to move into fix-and-flips and short-term rentals later is a great way to get hands-on experience while learning the ropes.From a tax perspective, each strategy has its own considerations.

Does bonus depreciation only apply to short-term rentals, or can you also take advantage of it with medium-term rentals?

If your long-term plan is to keep this as a rental after they graduate, then setting it up as a proper rental from the start can give you better write-offs and a smoother transition.In short: short-term = homestead simplicity, long-term investment = rental structure.

I'd be less concerned with weekday v weekend and more concerned about seasonality (depending on which national park you're talking about).Rocky Mountain National Park here in Colorado is a huge draw, and visitors come to Estes Park and stay in short-term rentals during the week, during the weekend, all the time ... but waaaay more in the summer. 

Found this:In the short-term rental world (like Airbnb, Vrbo, or local STR regulations), length of stay is almost always calculated by nights — not days.✅ Example:A guest checks in on Friday and checks out on Monday.They stay 3 nights (Friday, Saturday, Sunday) even though they’re there 4 calendar days (part of Friday through part of Monday).Here’s how each context typically uses it:🏨 Booking platforms (Airbnb, Vrbo, etc.): Charge and display stays in nights.🏛️ Local STR laws and zoning ordinances: Usually define short-term rentals as stays under 30 consecutive nights.🧾 Taxes and occupancy reports: Usually based on nights rented too.The only time "days" might matter is for insurance policies or local business licenses, but even then, they almost always convert it back to nights for consistency.Would you like me to check how your city or county specifically defines it?

So in short, what do you think are the best strategies in 2025 to consistently reach distressed sellers through marketing? 

Investment also spiked in Class A Short-Term Rentals (STR) and investors started paying higher and higher prices based upon anticipated STR rental rates, that exceeded sustainability based upon Long-Term Rental rates (LTR).

Santarelli, in two YouTube videos explains the promissory notes investment opportunity (Link), and mentions some of his other ventures including, “cannabis and crypto investing” and producing/co-producing six new Broadway musicals.

@Brittney Yang To structure a short-term partnership for your duplex investment, establish a joint venture or LLC with clear roles, responsibilities, and a timeline for dissolution.

I'd ask them if this is a short term thing or if they feel the place is no longer affordable and if no longer affordable let them out of the lease.