Buy and hold estate is a game won by those who can play the longest. 

For instance, I just had 2-hour conversation with a repeat investor client where we were analyzing a few properties on some very specific cash/cost-related criteria, developed a game plan for diversifying their real estate portfolio, and at the end, I was able to provide the data (without having gone into the conversation prepared to provide it) on what the average appreciation of a specific subregion has been the past several years and how that compares to the average for the area.

Now I know that wholesaling is a numbers game, and you want to keep your pipeline full.

As long as they are staying inside - playing board games, naked twister, watching movies, etc., no harm no foul.

You need to have "skin on the game".

And a bunch of old people are about to die, those folks don't need retirement housing in Florida, representing a drop in demand.I've got no skin in the Florida game, but the ONLY thing I'd hypothetically personally be looking at in Florida is detached SFRs with no HOA. 

He has reserves, but my feeling is many STR operators won't and will need to get out before a significant turnaround is possible.agreed on the STR  those folks are going to blow through their reserves or need to put their props into LTR ASAP for a year or so then come back into the game..  

It's a long game and you'll do fine as long as you go into it with the understanding that there are ups and downs. 

And even in the good days, they wanted some skin in the game. 

Lots of folks in this game tend to have mortgages up to their eyeballs which can really put the squeeze on.