In fact, I would want to go even lower because there's a very good chance some damage is hidden and costs will run higher than anticipated.If you aren't experienced, I recommend you just buy the good apple. 

Does the contract include a monetary damages provision?

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.

very sorry to hear that. a lot of "professional" unfortunately only look at you as a number and not a long term relationship. you should be able to put a complaint against home inspector to hopefully recover some damage they missed

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.

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.