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

Because it is an investment property, you would pay all fees, including appraisal.

Quote from @Chris Pontello: Hi Chris,Correct me if I'm wrong as I'm still learning creative financing solutions, but paying them some money would be if I could take over the loan.

Sometimes hard to find this happy medium in rate sheets, though.Another consideration would be taxes - points are typically treated as interest, so if your tax obligations are high this year vs being higher in the future, then this could also impact buying down now vs paying a little more in interest in future years. 

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.

There isn't enough cash flow in these deals to pay the mortgage, monthly expenses and the HELOC that I'm trying to leverage against.

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

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

Keep in mind you will probably have a deductable to pay first.

I would keep the deposit unless I am able to rebook the dates and then I would only make her pay the difference for any unbooked nights.