If you're not resident in Japan, you can't borrow from Japanese banks, and so that's out the window. 

I figure if the equity we have cash flows better than similar equity in a single family residence in Utah would, then we should consider this AITD as a serious option.

My plan was to keep the condo as my residence, but after a year, refinance to fund a down payment on a multi-family property, either out of state or in the surrounding NY area.

For our last single family residence we had a young married couple move in with a brother, all three applied.  

Avail sends this to the resident, collects rent and deposits it into our account.

I encourage you to interview property managers to determine what their approach looks like when managing properties for an investor who does not reside in the market where the property is located. 

If you own this as a rental then there is not homestead exemption and you'll pay much higher tax rate than a resident/owner occupant in SC. 

We recently relocated from our primary residence to a rental property ourselves (we recently welcomed a baby, and our house no longer accommodated our evolving needs).

None of these communities will be changing to residential neighborhoods, although a couple do have residential 'sides' that full time residents live in and can not be rented short term.Two of the big communities that you will have some issues with self managing are Reunion and Margaritaville.

And the first thing that came up when Googling the subject was Dodd and Frank, which requires RMLO if you originate more than 3 loans per year to a real estate buyer who will be residing in the property (Dodd Frank does not apply to commercial transactions, rental properties/duplexes and etc. among others).I know successful people who did this for a decade or decades.