If you believe it will continue to appreciate (like most of San Antonio), I would hold on to it even if there's a bit of negative cashflow for the first year or two. 

I also hope airbnb does not continue to get less host friendly.  

Do you think it will affect the types of deals they pursue, or will the demand for flexible financing options like private lending continue to grow regardless?

We're going to continue to add content at no cost to you.

I built my team through networking on places like BP forums and FB groups.I have since moved to Indianapolis from the west coast to continue to grow my portfolio here and have expanded my business to include support for other OOS investors who need the same support I did when I was remote.

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. 

And it's a rather low bar to get over for anyone wanting to continue to wholesale. 

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. 

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.