Maybe they would/could take it upon themselves to pay for the repairs to the roof to salvage your unit and prevent further damage then they would go after the HOA to recoup costs.

B) pay all the remaining rent but I’ll credit it against the kid’s rent next year.

If you tell the constable that you are concerned about damage, they may talk to him about leaving responsibly.If you are concerned about violence, have a means of defending yourself and let him know it.

After they book, it's still a good idea to use the platform app for communication because then the platform has a record of what you and the guest have said, in case you need it when a guest does damage and admits it to you, but later denies it to the platform.  

Granted, after 30 years the place is a pig sty, but if he goes quietly, no malicious damage, I would most likely return his damage in full. 

of course the sale of hurricane damaged houses also confuses the issue (my house had no such damage but is only about 4 blocks from houses that did).

The tenant understands that the property of the Tenant is not insured by the landlord for damage or loss of any kind (action of third party, fire, water, theft, vandalism, storm, heat or cold, electrical damage, pests, mold, accident, etc.), and the Landlord assumes no liability for such loss.

They usually have a process for filing a claim with the city for damage caused by them, and they may be willing to cover it.

Give her 30 days notice now, keep her security deposit, and send her a additional bill for damages to the unit in lieu of taking her to court for the damages.  

Next Step: With with sparkies quote, I'd get that quote over to sellers and with an amendment all written up ready for there signing giving me a credit at closing for exactly that amount.