I was actually pretty lucky in my 25 or so years of landlording. I think I had two tenants that screwed me for both rent and significant damage (one of them turned the bathtub on and moved without saying anything). Then I was screwed out of some rent a few more times after that, and of course the trips to the dump when tenants moved out and left half their crap behind.
Otherwise, most of my tenants were long term and took care of things. Of course I generally charged a bit under market rents and had a "don't bother me and I won't bother you" policy, which seemed to encourage the tenants to both stay longer and take care of little stuff on their own.
Same with my dad, though he's been doing it for over 50 years, and I've been slowly getting him to sell his rentals and get out of it. He just has two left now. The last rental house he sold, the tenant was furious at having to vacate and left a big mess. Not to mention purple walls and other crap that yours truly had to take care of. On the bright side, I found a decent sized pill stash behind the oven vent. Don't know what they were, other than most likely illegal, but I had a big smile on my face when I flushed them down the toilet.
It was good to do when I was younger and getting good tax breaks, etc., but now I just don't have the patience for it anymore, especially with how CA is going on regulation. It's just way easier to keep the money in Vanguard and take dividends instead of rent. Kind of going Galt out of rentals. :)