Checking to see what other landlords charge for damage

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He’s Moving at the end of the month and he  is moving out of state I take it with very limited money. My lease calls for a fine of $750 if you bring a dog in without permission and I found out 2 weeks ago that he had been bringing a dog over so I told him not to do it anymore. 
I heard today that the dog was back over there. He’s a little hot tempered so If he’s low on money I’m not going to charge him but want him to stop bringing dog over AND florida law says you have to send a certified letter outlining whatever you are going to keep for damages. He claims he’ll fix the hole but I have a feeling at the last day they’re going to be things I want money for 

How do you handle it with a situation like thatWhere he’s not going to want to wait for a certified letter and I want to comply with the law. what have you done in the past with a situation like that so he can get his deposit and I can collect for whatever isn’t done.