I would rather invest in safe markets that produce a good return, then I can use that income to pay for a vacation anywhere in the world.I'm very pessimistic about the STR market in Hawaii.

15% down with no STR experience - you're going to have to pay a price for that.

Each former member is then free to either do a 1031 on their % interest or take the cash and pay the tax.The opposite manuever was more common until around 15 years ago. 

I imagine this is a similar model to Redfin's associate agent program that pays by hour/tour.

Now, you need to figure out how to find deals and pay for them.

They didnt pay said task rabbit guy.

Not to mention, the right system will enable your tenants to pay rent online, have a tenant portal, and all the other features that both tenants and owners need this day and age. 

You shouldn't pay any draw until the work is done.

What I want is a way to have and trade the stocks and bonds I currently own at a large brokerage in an IRA (as well as ETFs preferably), but held (without paying extra foreign tax) offshore.

Pay off debt .