I don't know anything about your financial situation but I agree with James Hamling's comment that filing bankruptcy would be a very last resort and foreclosure only if you exhausted other options. 

If I'm in your shoes (which I was a few years ago) I would recommend attending at least 1-2 real estate meetups a month to start putting yourself out there and networking with other players in your market. 

nice resort. ive owned there for two years. 

Otherwise, bite the bullet and pay the real players in this area for what they provide (Buildium, Appfolio, RentManager, etc).

Once you befriend one of these big players, ask who they use.

Yes, he can still file bankruptcy, but that is only for a 30 day period (last resort.)Good Investing...

Here’s the thing though… 90% of insurance in Florida seems to be cheapest with Citizens (the insurer of last resort).  

That's a pretty hard situation to be dealing with in a remote resort area.  

I hear a lot about standard personal loans, mortgages, etc - but do banks or smaller players consider situations like the above?

Even Reagan had to resort to Keynesian economics to get us out of recession.