As an update, the property was successfully sold back on April after solving all HOA liens a judgements to my satisfaction.

....I've only had one full eviction in the past, luckily.  2- The one eviction I did have recently resulted in a judgement for me around $3000.  

Also I was advised if you bid full payoff at foreclosure auction in Alabama you cannot go after them for a deficiency judgement either.

Xavier Mike I have to start by saying I'd have to review your insurance policy to make any definite judgement.

I know nothing of the market, location, specific building and it's condition to make that sort of judgement. 

@Thomas Cundy it’s not clear exactly what you’re asking, but I get the sense that consulting an attorney on this would be a good idea.If you had to evict the tenant I think there’s a good chance you could ask for damages to be added to any judgement you got.A lot depends on the specifics of the situation, for example I don’t know whether you’d need to have something in your lease saying that the tenant is responsible for any damages done by guests or if that’s not necessary because it’s implied.I also don’t know what your options would be against the brother specifically.Assuming that no one is stepping up to fix the damage or pay to have it fixed, and you’re asking how you can get that to happen (and what your options are if they don’t), I do think it’s really a question for an attorney.Since it may end up relating to evicting your tenant, if you have a regular eviction attorney I’d recommend you start there.

Seller agrees to convey clear title by a general warranty deed, free of any liens, judgements or any other encumbrances.

As I mentioned, I have heard that protection has been weakened in Florida due to previous judgements, but nothing in law is black and white and I do not believe those protections are completely gone.

Send a certified letter requesting it and include the state law: If he doesn't respond accordingly file for a small claim judgement of 2x the deposit.

Also, I know if you have any judgements on your credit report such as credit card companies that took you to court and won and went into collection, you typically will be automatically disqualified from getting a mortgage.