But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

I'm betting he'd drive to that area.

I am confident price is your issue especially if you are deriving the price off a poor comp (smaller unit, etc) and then applying arbitrary adjustments.  

This was a poorly timed purchase at full retail so it likely is worse than virtually every other San Diego RE investor’s monthly appreciation. 

 - poor cash flow.  

I bet, when you started investing,  this day seemed so far off it was silly.

I see no value in it for evaluation.Realestate.com has always been a good site for accessing properties, but they do a poor job of evaluation. 

Not only is it very difficult but also leads to poor real estate investment decisions/ rejecting opportunities that require patience while attempting to achieve the W2 replacement as quickly as possible.

Moving forward scaling with hard money loans may be the best bet and would avoid the headaches of living in a construction project. 

You're best bet is to call a few brokers local to the area and see what they can come up with.It's definitely going to be a surplus or excess carrier that will do it and the premiums will be high.