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 suspect you'll have a hard time getting an attorney to assist you in an activity you're engaging in illegally.

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.

If you dated for months, really had an intention to tie the knot and even gave her an engagement ring, but it did not work out in the end... 

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

I would love to connect and hear about your investments and engagement with investor clients. 

I knew she was engaged but didn't know you were on here too!

@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.

Key to your approach, as you seem to already understand, is that it requires elevated levels of planning and due diligence, but with this approach, it can be a profitable strategy.As you are in the process of narrowing down locations, start engaging with local experts to best understand market dynamics and compliance requirements with local laws.  

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