I wont bore everyone with the details on that unless you want me too.. did not prep building for day of work - The comment above applies directly to this as well.. did not work out a solution to allow the work to be completed - Again, an assumption on your part that doesnt sound right, according to the OPs story.

That's a recipe for a destroyed house and vacancy by eviction.But that's just me.    

Example: if the wind blows over a tree and it smashes a hole in the roof, and rain water floods in and destroys the flooring, that should absolutely be covered.

I won' t take the easy way out and say "it's your responsibility to do your own due diligence".  

Would I spend all my profit on repairs and fixes after they destroy the home?

The former tenant believes he's being wronged, and wont let it go, he believes he has bent over a bit as a tenant, and the landlord should let it slide in light of previous "passes" they gave the landlord, and he may be right. 

IE 50k 100k.. to much work and I find those folks to be the most nervous to deal with.As well as I wont do business with anyone that wont fly to Oregon and walk through my new home communities to see we are real.. and meet with my banker and CPA and Lawyer .. its a well defined presentation and then sit back I don't do any selling.. in this area.. its not like selling real estate were you defiantly have to ask for the order and know how to ask for it.. 

If you run your system like this you wont be in the situation you are in. 

I would still smoke weed (but cant and wont) and chase my goals but I need a CDL to make my dreams happen.

It is more expensive but ensures you wont have issues down the road with tenants getting sick because it wasn't done right.