The struggle comes when you plan to sell, pay close attention to how the bank would treat the loan in the event you would sell.Even though its a bit more work, banks are typically open to these loans as it provides them with additional collateral in the event of default.  

95% of the time we get the seller to pay for the warranty.

Owning a duplex at 20 is a huge accomplishment, and it’s inspiring to see you’re already planning your next move.From my perspective, real estate investing is a long-term game focused on building equity, paying down debt, and maintaining stability over chasing short-term cash flow.

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.

Do you really want to pay these people to be the communicative link between you and your rental clientele?  

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

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.

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

I dont think I would have any cash flow from renting after paying me mortgage.

Pay off debt .