It's a smaller house so the premium for replacement cost over 10 years vs the actual cost of replacement in the event of serious damage might break even. 

The other part I didn't see mentioned is that you should charge the tenant 100% of this service cost for the repair assuming your lease makes mention of tenant caused damages being their responsibility.

Such as smoking or causing damage to the hotel room?

This is my old insurance hat coming out, but garage parking also opens the door to potential damage with mirrors clipping the side walls, issues with the garage door getting hit, etc. 

I’ve been inquiring about a reclamation clause since the land was not restored after 259 was built up. 

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.