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.

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.

You might talk with the realtor and feel "pushed"....like the seller probably already felt when you approached him (maybe?

I was also trying other approaches such as referrals.

I agree and follow the same approach as @Thomas Williamson by only having them in the living room and master bedroom.Unless you have tons of properties, then I don't think you will have too many issues.

This approach significantly reduces my workload and simplifies budgeting.However, I do have a six-plex where I cover the water expenses.