I think Brian ^ posted a pretty elaborate reply, so I will not say anything about Ko'olina or Turtle Bay.Generally speaking, doing a STR in Waikiki area is not the same as it used to be.

Would you mind elaborating on what happened? 

There are benefits to forming entities, but nothing as elaborate as what you are proposing and the reasons are generally more beneficial for business planning than asset protection. 

I probably didn’t elaborate well enough in my post.My income question was more meaning how do I know if it’s smart to invest in property with freelance income in a potentially volatile industry.

If you can elaborate more on what you are looking for, I can provide a bit more advice. 

and even had my picture taken with some dude in a Spider-man costume at a Kmart in Salem, Oregon.

This goes back to what I've been posting for a while and that's the fact most investors cannot articulate the risks they are protecting against or how these elaborate entity structures will actually protect them and there lies the problem. 

Hi Dmitriy,      Can you please elaborate on "investing in illiquid assets such as trust deeds and converting them to Roth at a deep discount."?

The majority of the  bigger pockets posters cannot articulate the risks or reasons why they believe its necessary to pursue elaborate entity formation structures similar to your your charts and ignore the action items that can truly accelerate your growth.

Could you please elaborate on what you mean by this?