I would guess that they have a paragraph clearing them of not finding a tank and limiting the damages to the cost of the sweep (Like a home inspection).

If you choose the applicant with the cleanest car, the nicest dressed when they met you, the best maintained current apartment, the stronger company they work for, it's one thing.

There will be a little bit of touch up work needed to cover and repaint nail holes in the walls (she did the place out really nicely but there are a lot of pictures and decor up on the walls)  Other than that there is no damage that I saw when I had to go in a couple of weeks ago to repair a leaky toilet valve.My question is this. 

Fortunately the carpet is new, so barring any disaster, I should be covered by tenant's deposit for any damages that occur in the future.  

. - Normally, that's how we handle things with our residential properties - disputes between tenants/subtenants must be handled amongst themselves unless leased property is damaged, or there is a non-payment issue.

(side note-she requested her pet deposit back and since the animal had done no damage, I returned it, with HIS permission)HE requests her off the lease but wouldn't sign a new lease; issue subsidesHE requests to sublease the unit-I do not sublease; issue subsidesHE states he is moving in with his new girlfriend and wants to break the lease.

I have a kind of an odd questions for fellow landlords or if anyone is in the insurance side.Last year when Irma hit South Florida, I suffered quite a bit of damages on a number of my rental.A particular one is a multi family building - I had fence damages, tree branch fell on roof, poked a hole through the roof, through the ceiling, debris everywhere inside, outside...so I filed a claim to my windstorm insurance carrier.I was lucky that the apartment the branch went through, was vacant at the time. 

Without bringing up the lease again and aggravate him even more as he wanted to talk to his attorney (according to what he said/presented he is a kid with rich parents with attorney), what some other ways to minimize the situation (ensuring no random security issue / damages on house and car), get my garage and driveway back, and get him to leave peacefully as soon as possible?

The owner also needs to apply for the short-term rental license and you need to consider liability, damages and upkeep.

If a property is properly winterized is there much risk of further damage due to freezing?