They are too close for comfortable game play.

Whether you go with an LLC or continue to own the property in your name, having good liability coverage is always recommended.

I believe Hawaii will continue regulating STR and it will be harder to make the numbers work. 

At the numbers you are talking about and where the market is heading you could pick up some very high quality NNN national credit tenant properties as commercial continues to recover. 

You can do this without bankruptcy and if you continue those new habits you can move on to buying an investment.

Until whoever is sending you these opportunities has the conversation with you on how much you'd like to make on a deal, how you figure your ARV and how you plan a rehab/ costs they are likely going to continue sending you opportunities you won't find too appealing. 

As far as I know the prices have continued to be stable or go up.

Personally, if your market tends toward the former condition (better/normal appreciation) I think it's a fairly safe deal looking at the long term, assuming infrastructure around you continues to support the idea of renting it.

And a single or double play is awesome.

Will we see home prices continue to beat year-over-year values yet again!?!?