@Robin Waters Yep I completely agree, if tourists and wealthy retirees are willing to pay more for things around here, they'll be expensive.

I am deeply interested in real estate to bring financial freedom plus generational wealth. I

If you’re already very wealthy, then pay cash for all your properties and call it good.

Yeah, except that's kinda investing-guru nonsense.Cash flow will not make you wealthy.

Well, people think they get rich buying rentals.. the real wealth is creating a company that can be sold !! 

Tom Wheelwright's book, Tax Free Wealth, is a good start for general tax info. 

From what I’ve been able to discern, he is fairly wealthy.

Because of this, they need the "defense" of cashflow until they build up some wealth...I cringe when I see completely inexperienced aspiring investors with no net worth on the forums talking about buying cashflow negative properties...according to them, it'll all pencil out "when" (not if) rates come back down, and "when" the property appreciates--as if those things are as certain as the sun rising in the morning!

"its a real business might not support it self day one with zero equity in it.. but its real and those that buy those assets are the ones that get wealthy .. far more than those that buy assets that do not appreciate or if they do very little but collect a few bucks a month which you know what happens to that it gets pissed away .

If you start off wealthy you need to start off with strong asset protection.