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.

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).

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.

While you may not make significant passive income renting the other side or the other three units, you can probably cut your living expenses in half or even live for nearly free in a 4-plex.If I had to do it all over again, I would have taken this approach at your age and purchased a 4-plex every year or so with minimal down payment.

We have a healthy rental market but if you are closer to the beaches even better. 

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.