Only time someone beats him is when the person being insured already has 3 or 5 policies with a given carrier & can get a volume discount based on that.Who he goes through for the insurance policies seems to rotate every few months, which implies to me that insurance carriers periodically discount their policies.

We currently run a RAV4 (our sole vehicle) with a custom hitch, 2 trailers, and a cargo carrier.

If your insurance carrier says to replace them then replace them.

We always strive to keep clients insured even if the carrier drops their coverage. 

The key is to purchase a policy from a carrier that is the best fit for your property.

I would suggest you go through an insurance broker, explain to them the situation and have them shop the policy with carriers that allow for short-term rentals.

Up to this point in my real estate carrier, I have done all the rehabs and work myself, but now I am looking to scale which means working with contractors.

There is a Umbrella carrier that only writes Umbrella coverage.

The insurance carriers based in CA are not the most competitive option, so a CA based agent will not have a contract with the insurance companies with the best pricing for rentals in OH, WI, IN, MO, etc.

Since the patient approach is not yielding results, and the lack of effective response by the Association is severely damaging her unit, I recommend commencing a lawsuit immediately, and making a claim on the insurance carrier, as she has an obligation to not let the problem become catastrophic for the building.