Ideally, we want the entire process to be managed locally to Hawaii to maintain authenticity and manage logistics effectively (stamps from Hawaii and not the mainland).Unfortunately, I haven't found a local company on the Big Island that offers these services.

It is not an authentic PNW beach town like Moclips and Longbeach.

Let's assume the property has $313,000 in NOIValued at 6.26 M 5% cap loan $4,695,000P+I annual= $413,400> NOI5.216M 6% cap loan $3,912,000P+I annual= 344,460 > NOI4.47M 7% cap loan $3,352,500P+I annual= $294,708 <NOI cash flow + Are you a gambling man? 

4 doors if managed right can make you, $350,000 over 2-4 years. 2 doors  maybe  $200,000 in 2-3 years.Little gamble. 

I told him I'd gamble that there's no one who even knows that restriction exists to enforce even if an heir lived in the area...the way to legally eliminate them is either get the beneficiary to record a new document (possibly a QC deed) to eliminate their restrictions, or pursue a Quiet Title if you think the person is no longer around or their heirs are not identifiable. 

So many folks will scream that buying negative cash flowing RE is "gambling".

It was definitely a gamble, because I was assembling furniture up until the night before their check-in :o I only had an opportunity to advertise on FF, because it was the first place we posted and it got enough inquiries right away.

It's more gambling than anything else.

However, the vacancy is really low in my area and prices are really high so it’s a gamble most house hackers take.

The alternative would be to find someone unlicensed/unbonded whish would be cheaper, but would be a gamble.