I also am keen on a second home in Kauai at some point in the not too distant future..Unlikely to be a BNB though.

It seems like one of those "too good to be true" things, but I have purchased 3 out of 5 properties that I currently own/rent out through people I know bringing friends, relatives, their distant friends etc.best of luck! 

I guess the real question I need to answer is, "Is there rental demand in the near and distant future?"

Distant relatives approached them about the property and they all independently came to a sales price.

So you need to treat both as long distant properties.

And offer #4 is a distant last place: The buyer could walk on day 29 if they are unable to secure financing with no consequences.

I have  800-900k in equity and have considered moving it into long-distant A rated properties with a more passive approach.

Like many of you, I am frequently contacted by syndicators raising capital for apartment building acquisitions in distant markets.

As the bad times become a distant memory in the rear view mirror, new investors are more willing to assume, debt, leverage, and smaller margins.  

I think it was 3 years before the Secretary of State would close it, but that's a distant memory.