I don’t want to generalize too much. Older places have their share of problems as well, but they are more of the “too much refinancing” type. The problems you mention – buildings without enough owners, HOA closing – these are more likely in buildings built after ’06, when things got really bubbly, and owners simply backed out or walked away. Either way, the HOA has to publish financial statements and answer your specific questions, and if they can’t, or won’t, well that’s a clear sign of trouble.
Moving, renting, moving again – it is a PITA. (My DW told me that my next move will be as a single man) It is easy advice to give but that doesn't make it any less worthwhile. A big advantage is you get to spend a year eyeballing the properties, the neighborhoods, local business, the traffic and also get a much better feel for personal security and local financial issues.
You can still do much of that from afar. Like Kroeran suggested – city data florida and other forums. Look at local bond issues – their credit ratings tell you so much. By now most of the financial issues communities are dealing with are out in the open - you just need to start reading local or regional press.
Just to be clear – I’m not trying to sell FL, but there aren’t any issues here that you won’t fine elsewhere. Don't know if prices are competitive but they sure are down a lot.
