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. 

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. 

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

What I would tell you is that as we built our portfolio we continued working our full time corporate (cubicle) jobs until we had 20 units (self-managing them along the way).

From my own personal experience and from others I think most reach the "tipping point" from self managing to using a PM somewhere between 5-15  units, especially if you have a W2 and want to continue to scale. 

As you discover opportunities, continue looking for the longer play!

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.

Seems like a very strict penalty if this is not followed through.The CTA provides that willfully reporting or attempting to report false or fraudulent beneficial ownership, or willfully failing to report or make updates to the reported data shall be punished with a civil penalty of up to $500/day while the violation continues (up to $10,000) and a criminal penalty of up to two years in prison.