You can add the per booking charge as a resort fee to each booking, then the guest is paying for the coverage not you.

While I have sufficient capital to undertake 1 or 2 flips at a time, the high cost of properties in the DMV area makes scaling challenging without resorting to interest-based financing.Is this feasible, or is it a stretch?

If you are buying in a resort or rural area it's likely an AVM will not be available and be too low in valuation to work.

Subdivisions, RV parks, resort-style developments/venues, storage, warehouses, small office, etc.

There are dozens of properties/resorts along the Grand Strand and they all have their own guidelines and quirks. 

“The liability for income tax ultimately can be fairly determined without resort to mere estimates, assumptions, and speculation.

@Taj Richardson we would be strictly equity players.

Im assuming most players involved in deals in your area are seasoned professionals.

It's vitally important to know who you are working with, and have the history of the players involved.

The Resort District is right at the end of the 264 corridor, where the bulk of the hotels are located on the Atlantic Ocean.