If you are paying cash for the STR this seems pretty easy. 

They must be very low odds because insurance companies are in the business of making money, not paying out maximums.

The tenant fails to pay their last month's rent and leaves the place needing new flooring and paint.

Our initial plan is to house hack a quadplex somewhere in Orange County.

And than the sob stories and how the nation should jump in and pay for what they didn't cover. 

If you allow service dog, you sure need to pay a deposit , application fee and monthly pet rent correct?

I don't know your living situation but if your paying x,xxx for rent or a mortgage and instead by living in one side and renting out the other you will be paying y,yyy instead and y is less then x that's great, especially if you can rent out your primary residence and make income there too. 

Investment Info:

Single-family residence fix & flip investment.

Purchase price: $58,500

Cash invested: $55,000

Sale price: $155,000

Contributors:
Peter Vekselman

Partner Drive...

We had an accounting system once that necessitated doing this - not ideal, but it keeps the assets and liabilities straight and AP is just an accrual until you pay the bill.

Throughout this entire time, I waited tables and bartended at night to pay rent.