Just a follow up question, were you utilizing debt to invest, I have always been taught since a young age to try and not utilize debt (I come from a family of stock market investors, traditional business owners) where debt is not utilized as frequently which I obviously understand debt can be a very powerful tool and utilized in a great way its just something I want to avoid with my investments to an extent any suggestions for investing without debt or as little as possible. 

You will owe monthly payments until you fix the property up, rent it out, and refinance to a more traditional 30 year fixed rate product. 

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

Can they be listed alongside other traditional MLS listings?

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

STRs in non-traditional vacation markets like Stuttgart or Wiesbaden aren’t t just about breaking even they’re re about creating consistent cash flow that also serves as a long-term hedge against inflation.5.

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. 

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?

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