Please note the information provided below is a layman's definition designed to provide a basic understanding for the general audience.

My main goal is to identify an opportunity that can be scaled from a couple of spots to a dozen, to several dozen eventually without the need to completely re-design or re-engineer the layout without respect to providing utilities. 

I have quite a few clients who self manage their vacation rentals from the mainland.Here is info directly off state of Hawaii website pertaining to vacation rentals (bold in mine):  If you’re off-island, you’ll need to designate a local contact who resides on the same island as the transient accommodation.

They can't be vague and are specifically designed not to be left open to the subjective interpretation of a fact finder. 

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

@Jagan ReddyI'm not a CPA or a cost segregation specialist, but I do know that if you are not designated as a  real estate professional, then you can only offset passive income by your passive losses.Qualifying as a real estate professional is more challenging than most people want you to think.

And since you are out of state you will need to be open to suggestion on design, size, etc.

Please note the information provided below is a layman's definition designed to provide a basic understanding for the general audience.

Yes, the Poconos area is saturated but I still believe if you buy the right property in the right spot and you invest in design and amenities, you will do very well.

I lacked the architectural knowledge to design my own.