If so, whats the story behind the house, why are you selling it?

Keep your fingers crossed for some cold storms mixed in ;) Now for the waves that is another story...this is when you see 10 footers crashing on some beach houses roofs. 

We couldn't go in and look at it directly, but I described the utility room and he looked at the condenser unit while he was doing an install on Property #2 (long story) and it came back very reasonable - $750, based on my description, but not firm since he couldn't see it directly.  

Here's my story: I have good credit and no credit card, auto debt.

There is more to the story but I'm it's hard typing on my phone.

"There's always someone in the neighborhood that knows everything you want to know...".There is definitely a story there, and more than one person knows it.

Does anyone have any success or failure stories? 

I submit that @Steve Vaughan is absolutely correct this is a very very dangerous play for the average person who has not demonstrated any ability to save money.. you just bury yourself in debt and if your deals don't go well... ( See many storied of first timers losing money) now your really Fubared ... you lost money and you have a mountain of CC debt which will absolutely hammer your once pristine FICO.Now if you have an AMEX black card with no limit or Very high limit say 200 to 500k well then go for it.

The point was that with the HOA, I have a risk of losing my house and currently my HOA doesn't seem to add any value by enforcing the nuisance rules, though I've heard horror stories about old ladies losing their paid off homes because of the wrong type of flowers being planted, etc.The HOA doesn't seem to add much value because they don't currently enforce rules but at any year that could change if enough people complain and it could swing the other way.

(The balance will be in Jamaica but that is another story and strategy)There is a lot of discussion on BP about investing for cashflow versus appreciation.