There’s a quiet privilege in getting to play games that aren’t dictated by the next quarter’s report.

STRs are becoming more of a specialized business model rather than a plug-and-play investment, and the people still winning are usually the ones with strong systems, premium locations, or heavy tax planning upfront.You’re not missing anything, the math has just changed.

Seasonal rent( Jan-March) goes for $4000/month On the other hand I saw another condo in estero, that is gated with a man, has a pool, a small storage, a gym, basketball courts, with HOA fees of $600/month with $900 CDD yearly that allows 12 leases with minimum of 30 days, condo reserve of 500k, built in 2003.

.: Don't play. 

Calculators play a key role in quickly analyzing market news and data, helping users understand changes, trends, and potential impacts.

Speed of course but the overall cost - points, interest rate, down payment - all play a role in financing a flip. 

Experience plays a role in all this as well.Cheers!

Zoning rules, short-term rental laws, HOA restrictions, and state-specific regulations also play a bigger role than many buyers expect, so aligning the intended use, financing structure, and local laws from the start is key to avoiding issues later.

However, we have an aging population (my mom is front-end Boomer) and as time rolls on, that demographic shift will inevitably play out and houses will be freed up for the next generation. 

But I’m personally not eager to buy more here, even with value add plays, etc.