I'm considering investing in STR in Hawaii to diversify my investment portfolio (mainly for capital appreciation) as well as it being a regular vacation place for my family.

But your main killers; road access, water access, fire hydrants, flood plain, storm sewers, Storm ponds, road surface requirements, etc. 

The main reason is that it is not initially set up for a Real Estate business like other “real estate-specific” accounting software.

If so and the monthly payment isn't too bad then you're still moving the needle forward if your main goal is wealth generation and not just cash flow. 

The main house will be house hacked for the first year and will turn into a co-living.   

Granted we only have 17 but still, I’ve never used anything except a simple excel spreadsheet and all my rental properties have a separate savings account under my main account at my local bank.

We are actually thinking about moving into the smaller unit. we are thinking if we should rent the main unit for long term rental or STR like airbnb but im afraid with airbnb, the non occupied days we may miss out on cash if its not rented out. 

Main goal of All In One heloc or 1st Lien Position Heloc:  Lower your daily average balance.Main Drawback: Rates are substantially higher than 60% of current 1st mortgage balances.If you are mostly living paycheck to paycheck and your money leaves your account as soon as it comes in to pay bills, this is not for you. 

This was not a complete rehab, we were keeping the main bath, moulding, and original dooors. 

Tools like this helped us determine that retiring in the Memphis Metro area was good for us and has helped form our investing strategy, mainly SFR and some commercial spaces (flex, studios, small office).