Some things that would be considered a great amenity are necessities (like a pool).

Not an amenity, but it will and does increase the frequency of bookings. 

That’s part of what drove me toward the luxury angle, catering to a niche market that’s currently underserved.Your point about local demand alignment is spot-on.

If you provide any kind of substantial services like catering, car service, etc you will change you tax situation and no longer can file under Schedule E.

I suggest having smart TVs and let them log into their own accounts, preferably with a guest mode so they auto-log out after a certain number of days.For catering to families, I would concentrate on providing amenities like puzzles and games. 

To me STR and hotel caters to different groups of travelers and so despite competition as long as the travel demand of Hawaii remains (as you pointed out is a robust assumption) I think both will continue to do well.  

With no comps in the area for new construction and the highest rehab selling for 205k, building enough at the onset, 4-6 new construction homes, may be the only way to start a neighborhood turn.The city is looking to increase density in the area and add anchor points in near the area to cater to future investment. 

You aren't offering any unique amenities.

Location and amenities are the two most important factors that bring potential renters to an STR. 

This translates to high rental demand and potential for appreciation.Diverse Opportunities: From bustling metropolises like Miami and Orlando to charming beach towns and vacation destinations, Florida caters to a wide range of investment strategies.