If not, I'd strongly encourage it. 

A successful short-sale typically benefits the borrower (homeowner) in the following ways: it can give them more time in the house (and payment-free); it is better than a foreclosure from a credit report perspective and wold allow him to obtain a new purchase loan for a new home in the future more quickly as compared to having it go through foreclosure.I would encourage you both to reach out to a local realtor with short-sale experience and have them facilitate the transaction, it would not cost you or the owner the commission as it would be paid out of the bank's proceeds.No, in a short-sale I would definitely not offer any payments to him directly that are not known and approved by the bank, you can get yourself in hot water and probably legal trouble by doing that on a short sale.

I see that you just bought a MFR property in the area - very cool and encouraging to see that happening right now. 

encourage you" to be sure that when the current tenant leaves that you rent the place out to another Section 8 tenant.    

Thanks for the encouragement on greys harbor.

Any thoughts/encouragement much appreciated....

@Andrew Kerr Thanks for the encouragement! 

@Brandon Abbott thanks for the encouragement! 

As for roaches, there's no may about it - a dirty person will attract and encourage roaches.

5) Are there any gov't assistance programs encouraging investors to supply Section 8 housing?