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.

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

However I'm thinking if I ever hit the windfall on something like this, their pockets are probably way deeper than mine and I'm not going to want to spend the money to fight it.

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

They were mean to him, training him to fight and be aggressive. 

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. 

Even as my portfolio grew exponentially, my work/life balance continued to improve.