I think the proper way is to "de-wire" the electric boxes, hang the drywall, pull the wires through the holes, reattach wires into the electric boxes and then push the rewired boxes into the hole from the outside in.

The home was in rough shape—think mold, a hole in the roof, and years of water damage.

If it did not I would have been in the hole.

Can anyone poke a hole in this approach ?

Over 4k in damages, utilities, past due rent, court fees, tons of trash, holes in walls, pee everywhere, etc. 

You could ad ST Louis, Detroit and any other crime ridden crap hole.   

I have an LLC but the hole is in my name.

In the middle of nowhere.And instead of a composting toilet, think about digging a hole (deep) and putting a couple of 55 gallon drums (with leach line if needed).

Then the rabbit hole started, and I learned the more I read about it. 

After applying the tenant's $1,000 deposit, you are in the hole $4,500.