Being out three months of rent plus $1,500, I'd be better off handing back their SD and forgiving the month of rent they couldn't pay.  

They had exhibited the desire to pay down debt and had cashed out the parks before us that had agreed to owner finance.

@Bonnie Low - it's important to know what services you're paying for.

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.

Billing is different for most and more than likely, you'll pay a retainer of some sort up front and have a balance due. 

If you are not planning on doing the management, and in today's world it doesn't pay very well for the time,  then you can look for the best market posable. 

You can't directly do something to allow you to sell the flip, and buy the triplex without paying gains. 

Unless the borrower is self employed and takes a lot of expenses to show lower income on their returns then it usually makes sense to pay a couple thousand a year in higher interest (you can pay like 4,000 a year in additional interest for DSCR if you are saving 30+k on your tax bill kind of math lol)

With the exception of building a trailer on the property (these are hard to finance), this sounds like a good plan AND if you are using it for your business AND your business pays more than 50% of the rent (if you have more than 1 tenant), then this is a more financeable property in the eyes of banks and credit unions as it would be consider a commercial "owner-occupied" property. 

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