Quote from @Kar Sun: This isn't right.The tenant should have liability insurance, which protects against accidents like a kitchen fire, a slip-and-fall, etc.

The members here on BP that talk about STR auto-run systems didn't install those systems and find dependable cleaners & handymen overnight.

Lock away extra supplies; trust is great, but accidents (or curious kids) happen.

When it comes to hooking up my follow-up system I've seen a lot of other CRMs fall short with drips (lack of good time delays, no custom mailing function, doesn't pause with a response, can send auto messages after a deal closes, etc) 

Since then, Chewy, Auto Zone, AT&T, Dollar Tree have all built distribution centers in the area. 

They like extra room to avoid accidents, etc....Just my $0.02....

By doing this, you are extending the policy's coverage to include your property manager, should they be held liable for any incidents or accidents on your property.Why is it important to add your property manager as an additional insured?

It sounds like the tenant has solid evidence their check or auto payment was received by the wrong party.  

But they auto-deposited $50 into my "marketing account."

A friend of mine recently got a $2M umbrella policy for around $300 annually by bundling it with home and auto insurance; it’s worth exploring.Out of curiosity, are you primarily investing in residential properties or venturing into commercial spaces?