With the cash flow play you need to buy low, negotiate hard on price, expect no appreciation and get a very healthy cash flow, nothing marginal,  And expect when you sell to make little to no appreciation, then any gains are icing on the cake.

If they don't complete the deal in 2 years, there is no messiness as their option period simply expires and the purchase portion of the deal is done.

@Mark SvendsenI would have given them to the buyer of the home at no cost.

We screen heavy and our tenants usually make great income, no criminal history’s, and are great tenants.

I have a credit score around the mid-700s, a pool of savings of $50,000, and no debt.

We understand that NO one can (consistently) sell a $345K sports car for half of market value!

The property needs a new roof, a new parking lot, and a few other minor improvements to enhance its performance.

I'm no fan of Section 8.  

One potential strategy to consider is waiting to sell the property until after you leave Japan, as this might exempt you from Japanese capital gains tax if you are no longer considered a resident for tax purposes.

Feels like no deal at the moment.