With careful planning, this approach can work well for you! 

There are plenty of reasons to title your real estate in LLC's but those who approach entity formation with anonymity as the objective are mistaken and usually complicate the entity formation process unnecessarily. 2.

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.

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.