Is there a desire out there to get more direct bookings, or is that considered too complicated?

I'm curious - what is driving the desire to reduce premiums?

Pretty desirable for renters - not everyone wants to share a wall between their spaces with neighbors. 2.

I really like his desire to be as efficient as possible owning as few rentals as necessary.  

Your post is very vague.What are your dreams, goals and desires?

They have higher HOA and taxes than other established neighborhood and I was wondering if those are desirable for rentals or resale later.

Include maintenance, vacancies, and capital reserves from day one.Learn landlord-tenant laws for NY early, especially for Hudson Valley—this will save you headaches.If possible, live in the least desirable unit and improve it last; that maximizes upside while you’re there.House hacking is a powerful way to reduce risk, learn property management, and build confidence before scaling.

I live in South Louisiana but I have no desire to focus in this area. 

You can also consider areas just outside of desirable markets.

Many desirable areas for long term rentals with great public schools in Baldwin County.