Holes in walls, removing wall paper, dark trim etc.

Basically I want to make sure that I have a strongly worded addendum to discourage any tenant from drilling holes, painting, or destroying these beautiful historical beams.

We vacated the property on Nov 16th, had a physical walkthrough with the landlord noting only a small hole in the living room drywall and ZERO damage or concerns otherwise (we only lived in the home for 5mo). 

She had actual holes in the flat roof from that, with massive water damage and two units currently uninhabitable.

I realize that this is a massive black hole without more details but let me say that the school is fully structurally sound.

If you have plenty of cash to bail yourself out of a hole (evictions, trashing the place, etc.) and still be able to make the interest payments then it might be a reasonable option.  

Mine was just old & scratched up, not cracked or have holes in it.

I've recently gone down the rabbit hole of investing in real estate while attempting to join a friend as a partner on a deal.

As you might have noticed, there are drill holes all the way around the house, which I'm guessing might be from them filling in the blocks with concrete at some point. 

After I move out of my money hole (apartment complex), I will put funds to the side to start a Direct Mail Campaign.