Based on my research, in Pittsburgh, the school board tracks sales of homes and if there is a significant discrepancy between sales price/current assessment values, they will appeal and you get a higher tax bill.

There is likely a phone number and persons name that will come up, that you can reference, since he is having bills that arrive to the mailbox and packages to the door with his name on them.You could make it a pre-condition to the seller that he allow a background check on the tenant before closing and your offer is contingent on your approval.Neighbors typically know what's going on in the neighborhood and will know who the guy is and if he is a trouble maker.He probably has a car and a private detective can run the plates.And so on.The information is readily available is the knowledge is worth knowing.

I would simply prorate the cost and bill the lost warranty value back to the tenant.

You can also bill them for the additional costs for leasing agent, listing, etc if you have any of those. 

Is it wear and tear or is it tenant caused damage that you can just bill them for now?

Once GP f**d up in their DD, the bill goes to LP, then they would issue capital call.

Technically I could line up a replacement job and let that pay the bills while I invest slowly (and that’s definitely one of my contingency plans) but in some ways that does defeat the purpose, since leaving the corporate world and focusing all of my time on an investment business is probably the biggest appeal for me.

For those who have tried Airbnb long term rentals (typical more than a month), how do you factor in the utility bills?

That means don't put bills in your personal name or have anything that would indicate on your credit that you used that address as your primary home. 

Quote from @Bill B.: LISTEN TO THE EXPERTS!!