We found that two key factors significantly helped us succeed with our short-term rental (STR): using NightlyPricer instead of AirDNA and opting for Safely Insurance.NightlyPricer: Rather than relying on AirDNA, we chose Nightly Pricer, which provides more dynamic, real-time adjustments based on demand, local events, and market trends.

There are risky, but high return options like QQQ which grew 27% over the last year or on the other side / safe end, there are super secure short term US government bonds like SGOV which pays out about 4.5% in dividends. 

We bank with Chase for our big transactions. 

I would rather invest in safe markets that produce a good return, then I can use that income to pay for a vacation anywhere in the world.I'm very pessimistic about the STR market in Hawaii.

All the add-ons are a la carte so you can definitely get a lot of value based on what you need.One thing I personally don't like is that when tenants pay rent, they are charged $1 per transaction for ACH use.

We couldn't see the floors (too much trash), but probably safe to assume those should be replaced as well.

It always better to be safe than sorry, but the building dept will let you know what the best course is.

Meanwhile, the sellers who are most likely to offer creative financing are normally the owners of  real estate that have issues.....condition.....low barrier/over supply market......or perhaps pricing issue, and one of these factors is why its not marketable in a arms length transaction and why creative financing would be accepted.

Option D: you are considered a "disqualified person" to your IRA and as such are prohibited from engaging in any transaction in an IRA or receiving any benefits from the IRA (directly or indirectly), therefore I strongly suggest you avoid this option if you wish to stay out of trouble. 

It may be helpful:I can give you some general info on insuring the property:Here are some things to look for from an Insurance prospective:1.Any in-ground tanks (active or inactive)2.Any Knob & Tube or Aluminum Wiring3.If built before 1978, does the building have Lead Safe certifications4.Any wood stoves or secondary heating units.