There is also the question if all of this is even necessary, Nate has asked on a lot of posts if anyone has ever had a claim above their insurance and umbrella and at least from what I have seen no one has responded that they have but would be curious if you did what were the circumstances.  

The umbrella starts when the limits of the underlying policy are exhausted for a covered claim. 

In essence, if you don't live there as your primary residence you can't claim that exemption and get mangled. 

From a claims standpoint, short term rentals statistically have a higher claims and pay out rate, so the insurance is more expensive.

@Michael D NewcomerMichael, I am not claiming that you are a "butt in the world" but "The road to hell is paved with good intentions". 

Travelers is just denying claims right and left. 

They can deny claims based on the Misrepresentation clause in policies if they find out the property is not your primary residence.I'll send you some info on who my flippers use.

If you have multiple properties, then you will need to decide which one to declare the homeowner's exemption against (you can only claim one) and notify the county assessor of any changes.

When a tenant claims the house was filthy or that a door was damaged before they moved in, I have picture evidence to show otherwise.

I take pictures of rentals when they move out and just list cleaning and repairs individually on the notice to make a claim on the security deposit.