Yes, there are LLs who make a good living serving this niche market.My husband retired from being a mental health case manager for more than 30 years in the south Puget Sound area. 

Also he wants to get both of his properties out of his name in case something happens health wise. 

You may want to check on the health of the HOA, though, to be sure you're not about to be hit with some stupid high assessment. 

If it gets to it, the threat of a complaint to real estate commission is pretty powerful in TX so maybe it’s the same in FL.

Yes, absolutely yes, review items such as crime trends, median income, unemployment figures, non-farm payroll figures and growth respective of that, school system health, general GDP growth of the prospective market.

And for the 30 year tenant, it's easier for you to tell them, sorry, "mom is in bad health, we'll have to move her" and it would be less awkward and a good excuse.Sounds like a real headache to fix, especially after years of neglect, so just get rid of it, and use the proceeds to buy something more up to date.

Assuming the kitchen and bathroom in place are functional, complete, and absent health/safety hazards, certainly. 

This type of behavior triggers numerous phone calls to their Quota and after a while, they will begin to see the threats. 

Pics of the vehicle, pics of him, and if he lays down any sort of personal threat like, "I'm gonna (whatever)" you're on the phone to the police immediately.The only thing I would add is that you should probably send your husband in alone for this one, or have him go with a male friend. 

You have options but threating to sure him is not a viable one.