He has each one listed for $100k UNDER what he owes on them.

Hello BP, I saw this in one of my FB groups and wanted to share this in the event you were affected - "I’ve worked as a full time licensed claims adjuster for years along with being a STR owner in Tennessee.

@Kerlous TadresHey Kerlous, first of all thank you for taking some time to reply on my post.

I haven’t dealt with one on any of my deals while in my time lending but on the residential side gap funding comes up on a weekly basis.

This is our first time with STRs, and we’re willing to learn.

We charge one month rent and one month security deposit before move in (make sure payments have cleared before turning over keys)  One month security is max allowable by Delaware Landlord Tenant code.If they have a pet you can charge a pet deposit (again, by state code, DE you can charge up to 1 month rent)If separately metered utilities, make sure they've transferred them into their name by providing account numbers and also a copy of their renter insurance before move in.Good luck!

I am considering having him book in 1-2 weeks at a time.

Any paper trails that should be in place or is it as simple as giving notice at the right time next year and not renewing the lease?

They can ask you to serve notice so one unit (or both) are vacant at the time of possession, but if you agree to that make sure you have a large deposit and some of that is not refundable if the buyer backs out as you will need it to cover the lost rent.

You'll only need one policy.