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.

The garage and the fact that a long term tenant was in place paying market rent.

It will pay off. 

Their "Titanium Service" does NOT mean anything, other than they would ask you to pay $10K to sign up for it.

They sent a new contract trying to bind me to still pay $200 per month, which I refused to sign.

You've got to include loan pay down, appreciation, and depreciation in your return calculations.The point of cash flow is to keep you safe.

Namely, that if a tenant (in this case accompanied by a whole family) ends up stop paying rent and I would be on the hook for both covering the mortgage and dealing with open ended legal costs and time.

Quote from @Cameron Moore: Exactly. 15 years ago, I noticed an increase in owners using insurance to pay for a replacement roof, usually to sweeten the pot during a sale.

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

The flipper pays 12.5% interest to the lender, and I receive 10% of that.