If this is likely the cause for you, most carriers will deny this type of claim anyway since normal wear and tear is a typical policy exclusion.  

most carriers also differentiate between short term rentals and long term rentals. 

Other carriers will not give an umbrella over many entities like my scenario;  solo-401ks, LLCs, personal etc, its a mess.Best of luck, curt

My first concern:  Is it likely that my insurance carrier will drop me if I file a second claim?  

Preferably they should be licensed in all the states you operate.If you have multiple policies with multiple carriers in different states, that agent will need to shop the Umbrella coverage.  

Hi - I can paypal, venmo, carrier pigeon you the funds - would love to find a BPCON ticket. 

Most Insurance carriers will only write Owner occupied buildings on a Homeowners Policy

The camera's really help but ultimately it is the responsibility of the carrier to properly deliver the package.  

The underlying theme of the LLC is the fact that if someone has a death or permanent injury on your property and they sue (which they will), your risk would be limited to the assets and cash held by the LLC, not your personal assets and cash.But in either case, your insurance carriers have a duty to defend and will fight to minimize your loss.  

The case was completely frivolous and went nowhere (in fact, my E&O insurance carrier countersued the tenant for the legal fees and she ended up with a new collection on her record).