I would think a more nuanced marketing approach where agents compensation is based on achievable results and other factors (e.g., hours committed to representation, achievement goals, discounts for properties based on price for square footage, negotiation of post escrow discounts, credit for seller/agent cooperation, transaction coordination commitment) might be more digestible for a buyer.Should be interesting to see going forward, but I do think in general, agent compensation will be less as things develop.

I've spoke with the folks over at Abodea, who do offer a scalable call-center approach to HOA PM at quite affordable rates, but we're still missing the kind of local, on-site general contractor/handyman or capital management planning schedules that would be required for proactively addressing homeowner and community association needs. 

Lenders who understand and specialize in such properties can be more flexible with their criteria.One approach is to ensure you provide comprehensive documentation on the property's potential and zoning specifics.

There is a BP RE investor who uses this approach as one of his primary acquisition strategies.  

This approach helps protect against potential complaints.

Yes, I know.Assuming it is a sale, your approach is not how it works.

Your approach of setting up separate LLCs for each property under a holding company is a common strategy to limit liability and protect the equity of each property individually.

Approach sellers who might be open to owner financing – especially in a small town where personal connections and negotiations can go a long way.Short-Term Rentals (STR): Given the touristy nature of your area, an STR could yield higher returns than a long-term rental (LTR).

I need advice on the best financial approach for this situation.

A much better approach is for the executor to directly sell the properties out of the estate.The taxes will be paid at settlement and your girlfriend will receive the proceeds.