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

Tenants all tell me they'd much rather rent from an individual landlord, the big PM companies have bad reputations apparently.

When exploring financing strategies for your first BRRRR project, especially with an owned property, start by researching reputable private or hard money lenders who specialize in rehab financing (like us :)).

Damage is damage.

There are companies that sell turn-key rentals that could be a great solution for a busy professional, or maybe finding a reputable wholesaling company or realtor to help bring you deals to leverage your time better. 

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.  

Steps to Vet a Hard Money Lending FirmReview Their Track Record:Look into the firm's history and reputation.

-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).