im based out of Fort Lauderdale but I help a few clients in the West Palm Beach area.

South Philadelphia's base zoning districts are not very accommodating either.

The first people that lose their money in a downturn are those that are lending at insanely high LTVs without adequate underwriting experience including determining if the borrower's qualifications based on credit/character, capacity, and collateral.  

Far too risky and unlikely to succeed.It's unclear what the $2,500 monthly payment is based onAny one of the owner or mortgage or lien holders can force the foreclosure of the property.

Since construction loans fund their draws  based on completed  work, having the additional capital to advance the construction progress is helpful.

You won’t end up in tax court but if you do, you would win based on everything you cited about material participation as long as you have a time and activity log that shows your tasks and provide a guest list that shows the number of nights your guests stay (easily found on the various platforms). 

We have a small fund based out of florida.

I expect if the stock market truly crashed long term the government would bail out 401Ks before STR investors based on the government's previous actions.

I'd argue that both HELOCs and CES have good utilization for both short/long term plays.

Instead, a lender will want to see that the property currently brings in (or has the potential to based on market rents) enough to cover the monthly principal, interest, taxes, insurance and HOA (if applicable).