You care about the cash on cash return, they’ll care about the debt service coverage ratio (DSCR).

It’s different than umbrella just on your vehicle though... you list every asset that brings the risk, car, boat, property, etc and they price their risk accordingly - but it’s all risk coverage generally speaking. 

Luckily, he had coverage for the fee gap in his insurance policy but it was still a shock. 

I put in bids for 2/2s in desirable areas/resorts that were expected to gross about 65-70K and it was just insane: people coming in with cash, waiving appraisal contingency or providing gap coverage, etc.

For each property have her gather 1) does she have forced insurance (lender provided) on the property 2) what was last date of coverage. 

If the policy has Replacement Cost coverage the payout will be a two part process. 

The starting place is the Building coverage.  

For property insurance, just make sure you have enough liability coverage.

Also, I'm starting to heavily favor negotiating for a home warranty coverage during the sale for investment properties since the warranty company covers (to some degree) many of the highest value systems of the house during the first year or two after purchase, leaving time to build up reserves.

This policy goes beyond your standard liability coverage and you can add millions of coverage.