@Michael Baum You are right in saying that if guests break $2000 worth of stuff in a year, we have the wrong kind of guests.  

If they support a rent increase, you could look into raising your rents by that amount to offset the cost.

Thank you for your kind response!

Personally, if your market tends toward the former condition (better/normal appreciation) I think it's a fairly safe deal looking at the long term, assuming infrastructure around you continues to support the idea of renting it.

You don't want to start playing sides here and getting involved in these kinds of debates.

What kind of insurance do you use? 

I’m willing to volunteer my time to assist with tasks, research, or anything that supports your business while I learn the industry.If you’re open to mentoring someone hardworking and motivated, please reach out—I’d love to connect!

I work (kind of) with a few GCs.

You are very detailed about your complaints, but never mention basic important details such as what kind of rental agreement was given to these tenants?

I've just been reading Nassim Taleb lately and he talks about this kind of situation all the time.