What damage could it possibly cause that their security deposit wouldn't be able to handle, worst case scenario? 

They forced the back door open, (you could see the minor damage to the back door), then went inside to the front door, removed the entire door lock and went off to have a key made, then they reinstalled the front door lock.

Guest Damage Insurance...This type of insurance covers small damages (no more than several thousand) that guests might do to the property.

Damage is damage.

If not, she will eventually find a new place, stop paying rent, string you along, and then move out in the middle of the night leaving you with a vacancy, past due rent and most likely a mess and damage to the unit.  

-As to rent payment, in Florida, a tenant would either owe liquidated damages (as stated in the lease or would owe rent that accrues during the lease term until such time as the landlord is able to re-rent the property on their account.

Normally, if the policy values the loss on Replacement Cost, they will initially pay the loss at the Depreciated value, once the damaged area is rebuilt, then they pay the additional amount (up to the limit on the policy).   

Looking for a rental after 13 year, he may be in a bit of shock at the rental prices, but that's his problem.As for damage deposit, you can only keep money for damages that you know he did (ie anything since 2022). 

Let them leave, repair any damages they did (from their deposit) and get it rented to the next tenant after you find out a few things. 

The reason for selling is because the home has been a money pit (major tenant damage) and a revolving door (tenants leaving).