The appraiser will ask for permits for the work done, and if there is non to be provided he/she will not give the value and in turn you will not be able to get the full amount of money out of the home you were hoping to get.  

In your case, it could make sense to setup a series LLC to isolate each property.

To respond to some of your other points. 1.

If either of them were to stay involved, it could cost you money and you would collect less.Send it to collections yourself.

I've played around with the idea of giving guests a YouTubeTV login but that seems risky.

1) I always use zillow to list new properties and use there platform to accept zillow applications2) Doorloop for management that includes accounting, repository for documents like leases, collect rents, tenant communications3) Received lease agreement from a lawyer

It seems weird to post the exact same thing again.https://www.biggerpockets.com/forums/48/topics/1220392-what-...

If they're like the other relocation companies, you can ask to background check the tenants.

Are you trying to deter theft, vandalism, other crimes?

Another option here could be to buy down the interest rate a bit.