The county/city zoning board has said this unit is not an issue and is grandfathered in, but he's worried about the more stringent FHA appraisal/inspection3) Buyer "skin in the game" - doesn't want to be left holding the property again as this has happened to him at least twice on previous land-contract/CFD arrangements4) Ability for buyer to acquire traditional financing at balloon5) Effective total cash to the seller is a primary driverWe submitted an offer that solves all these problems:Property A:Purchase price: 360k using FHA loan, owner-occupiedProperty B:Purchase price: 305k, 0% down, 25 yr amortization, 5 yr balloon, 4% interest rateNote + mortgage arrangement with professional loan servicing/escrowAssuming a 9% annual return in the stock market, this arrangement is equal in total cash to seller (including accounting for inflation,etc).

I thought about using a contact from the web ... but is that safe?

If so, I realize my post is late to the game and wish you the best, but wanted to share a few things and maybe reassure you or give you more clarity of situation in Hawaii and submitting an offer in this market.  

I figure the stepping stone approach may be best suited for my game plan.

I have never played the "guess what this is" game with tenants.

If you cash out refi and use it for a down payment, the game is over after 2 deals until you build up enough equity to jump back in.

Really stand out and change the local Airbnb game.

You got in the game earlier, but had some scaling restraints.

It’s a patience game with this property but I’m pumped!

Go to REI meetings and see if any investors want to get out of the game and want to sell their properties.