They continue to add features which has been helpful and welcome.

I have been with a property management company for 2-3 years in Arizona and the property is being run continuously at a loss.

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.

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. 

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

Successful individuals must learn to accept uncertainty, maintain a flexible mindset, and continue to invest.

Quote from @Stuart Udis: As I am sure is the case with many investors, my residential and commercial leases continue to evolve.

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?

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).