It takes time but worth it.How do you plan to finance your first property—are you looking at traditional loans, or have you considered other options like house hacking?

A couple of years back they even cancelled holiday lights traditionally displayed in a large local park.

Can they be listed alongside other traditional MLS listings?

Is STRs the way to go in Hawaii or maybe just traditional LTRs instead? 

I hear you, I think the price of turn key STRs are almost impossible to make money on in the traditional markets. 

-> Funding: you can consider as options mortage brokers who can scout/compare the best offers in the market and you can also consider public funding programmes that exists as an incentive to renovate and bring houses to the market, either for tourism or traditional rental.As an example, on the traditional rental there is a funding program ("Arrendamento Acessivel") that funds up to 90% of the project and can be used to cover part of the renovation costs, as well as, part of the purchasing.

I agree that DealCheck (or the BP calculator) does not provide enough tools or functionality to analyze those types of transactions (yet).But I would argue that it does a great job at analyzing more traditional buy & hold SFRs and multi-families, as well as flips and rehab projects. 

The idea is spreading, and could spread to some other spots here that have traditionally been STR friendly. 

Two of my units will be vacated in the next 2 months so this is a good time to consider this over my traditional 12 month leases again. 

I have used both Traditional (pre-tax) funds, Roth and HSA.