I'm not trying to chase you off from investing in Florida, but instead inform you that there is a small gauntlet to run, in addition to the HOA-and-condo concerns.

It's about synergy and shared goals.I had a friend in a similar situation who felt like she was always chasing her agent.

Meet the players. 

I had turned 40k into 300k, and then lost it all plus another 100k chasing my losses.

Although in my experience, people are chasing rainbows and not willing to put in the work of it all. 

His family is a major player in the affordable housing market and new developments.

I got un-renewed by my old ins and rejected by almost all ins companies (except for some crazy ones quoting me 10k/year) on my primary house, which is far from any fire zone but I had 2 claims on my 2 rentals (I am a small player so under my name not LLC) in the past 3 years so I got fked. 

I would suggest that all the big money has been chasing mobile home parks for at least a decade or more. 

Remember, no system is perfect, so avoid the temptation of constantly chasing after the next shiny object.

You will spend more time and money chasing pennies than focused on the dollar bills.