Ask for a Sellers Disclosure  

In Florida a seller of residential property is obligated to disclose to a buyer all facts known to a seller that materially and adversely affect the value of the Property being sold which are not readily observable by a buyer. This means that they have to tell a buyer about any issue that would reduce the value of the property or make the property less desirable.                                                                                                                       

Are there any special assessments

 These are extra fees that are charged for a specific amount paid in full or over an extended period of time to cover any condition like roof repairs, fund reserve account, major building repairs etc.  Sometimes the homeowners association require the seller to pay the amount in full at closing, and sometimes the buyer assumes the unpaid balance.                                                                                                                                        

Does the community have a reserve 

If there are no reserves, then the possibility exist that the unit owners could be assessed a special assessment to fund the reserve account. This could possibly end up being a very large amount.                                                                                                                                                              

Does the community have homeowners insurance

This is crucial because you are making a large investment which should be insured.  Anything can happen.  This insurance usually covers the building exterior and the roof, among other things.                                                                                                                                                                   

Are there any rental restrictions (If its an investment property)

Some communities have no rental restrictions.  However, some do restrict when and for how long the unit can be rented.  Example, no  rentals for the first year of ownership, no rentals for the first 2 years of ownership, no rentals allowed, unit can only be rented 1 time per  year etc.                                                                                                                                                                                                                                               

Ask for  a copy of the budget

This will show the income and expenses for the community and and whether or not they are actually meeting their financial obligations.  This should give you an insight as to whether a large special assessment might be coming in the near future.                

Ask for a copy of the minutes from the last 2 or 3 meetings

This will give you an insight into the community and its operations.