Any sort of surface damage: holes in drywall, carpet stains, damaged blinds, etc. 10. 

Only 1 win's, the a-hole lawyers searching for there next sucker to sue.

For example, total pollution exclusion that most policies have now....lets make an extreme example and say your tenant decides to start pouring used motor oil into a hole in the ground in your back yard.  

Or are holes after move-out just part of the cost of doing business?

Highly recommend you share more about the research YOU have put it into your dilemma, so we can poke holes in it, add to it, etc.

Now you have to evict as this A @#@HOLE has rights.  

If nothing else, you've given me a rabbit hole to go down. 

Which might poke a hole in anonymity???

However, the financials seem challenging, and I’m seeking advice to make this viable without significant monetary loss.As a side note, I’m quite the handyman—think ‘handyman on steroids’—so I’m open to properties that require some elbow grease.Any strategies or insights from the community would be greatly appreciated!

If there is a leak, the first thing that should be done is to cut a hole in the drywall or plywood to get the wet materials out.