The only thing I know of that is restrictive about Florida rental rules is that there is a tax, like a hotel tax, on short term lets. If the rental period is more than 6 months, there is no rental tax.

Some of the insurance companies have decided to stop issuing policies in Florida. It's possible to get an insurance binder on a property before you own it, that says the insurance company will issue a policy on the property.

It's easy enough to talk to a couple of insurance companies before buying. 4-5 minutes spent on a phone call is pretty cheap. Then you make your purchase offer contingient upon being able to purchase insurance. Then, if you can't fond insurance, the sale is cancelled.

Florida isn't my favorite place. I don't like the humidity, the bugs, or the crowds. But if you like the place, it is a good time to buy. There are foreclosures that can be purchased as short sales (for less than the mortgage owed on them), and sellers have dropped their prices and some of them are accepting very low offers.

Yes, it might take awhile for the market to recover. But real estate is a long term investment, and the goal is to buy low and sell high. If you only purchase in really hot markets, you aren't going to get the low pirchase price. Also, real estate runs in cycles, so if you purchase when the price is high, there is nowhere to go but down.