One of the most important aspects of wholesaling is determining that the seller has the authority to sell the property.

., in favor of any governmental body, authority or agency.

If multiple neighbors contact the property owner or local authorities, it might increase the pressure to resolve these issues.

It is the role of the legislature and municipal authorities, not the courts, to consider any policy concerns related to STRs.

Does your local housing authority allow this type of arrangement? 

My challenge is that I am not authorized/signed up with the city to take on CHA checks, so that will take a while to get a tenant.

If it is a COA, F.S. 718.116(8)(c) provides:(c) An association waives the right to collect any moneys owed in excess of the amounts specified in the estoppel certificate from any person who in good faith relies upon the estoppel certificate and from the person’s successors and assigns.If it's an HOA, F.S. 720.30851(3) provides:(3) An association waives the right to collect any moneys owed in excess of the amounts specified in the estoppel certificate from any person who in good faith relies upon the estoppel certificate and from the person’s successors and assigns.Now there are Master Associations that have an HOA, and the MA has condos built inside them with a separate COA, so some condos can have two assessments, one for the HOA and one for the COA. 

We want to ensure the property is safe and habitable, but these expenses seem excessive.

A closing / title company can handle the transaction but may want to get a lawyer to draft the documents.Assuming you are buying in your name and not a LLC - if a LLC then there would need to be additional docs like a authorization for LLC to borrow $ etc

What authority under the Trust does your father have to sell the property?