I am attempting to eliminate as much "known" risk as possible.Best of luck to you!

I have changed my buy criteria in an attempt to account for the increased risk, but did I change it enough? 

I have changed my buy criteria in an attempt to account for the increased risk, but did I change it enough?

The tenant attempted to give notice leaving to San Francisco about 2 hours north, and leaving the house in possession of the squatter, even though she called the police there is nothing they can do because of the squatter rights.

Many years back an attempt was made to allow it to be done in Florida but the Dept of Insurance opined that would be issuing coverage on a casualty basis which is prohibited and so refused to allow it. 

Compass isn't a discounter but they have thrown so much money at the business in an attempt to buy it all, they too are laying people off. 

Landlord may place signage on the Premises or show the Premises to perspective renters or buyers during the last thirty (30) days of occupancy or any time the property is listed for sale.When she failed to let the contractor in the second time, I texted her to let her know that we would schedule a third attempt.

Should I attempt to get my $500 back and if so what would be the suggested way of going about it or just let it go and lick my wounds?

Be safe and keep a healthy body! 

You should attempt to estimate the average to remain competitive, and then any overages could be factored into rent or surcharge increases the following year, assuming you were not extremely far off in your estimates.