The tenants are a couple of young  brothers who I'm finding are treating the house as an apartment an do not realize they have some responsibility in maintaining the yard and reporting any leaks or damage. 

So he’s causing no damage to my property

We fixed a couple damaged windows, and painted the cabinets with new hardware through the entire home.

If they feel that they gave you a discount (whether real or based on false assumptions of market value) then that could damage the relationship.There are definitely benefits to both buyer and seller in doing an off market sale like this, just make sure they have all the information you have so that it stays above board.Good luck!

It looks structurally sound in the outside, but it has holes in the roof, floor, and theres a lot of water damage in the inside.

I would explain that she would be on the hook for damage to the kitchen flooring.

@Dom Battezzato   So what can you do in this situation where your damage/cleaning deposit is less than your typical long term renter?

Their $1mil protection covers damages that you can show proof was caused by the guest.

However, this does do a bit of damage to my reputation and that's the last thing I want.

Can’t tell you how much money I’ve made working for clients in the last 18 years dealing with pet odors and damage.