Just be anything but "The Owner," because no good will come of it.That said, here's what I'd ask:"What do you like most about living here?""

Try local goodwill or used construction material store for fixtures, appliance, things the home needs but you might not want to buy brand new.  

If you pay him, you won't gain any goodwill, you'll just be donating to charity.

...Mentioned on the phone last night that he's out the commission if the deal doesn't close & would rather have the goodwill and his reputation in his small town.)  

(He lives out of state, but has occupied the house in the past)  So all that being said, at what point does my persistence become an annoyance and potentially damaged my (remaining) goodwill with my neighbor? 

I took trailer loads to the good will, and now have fellow who will clean up the rest for the value of resalable useful items (I have an old tractor, useful appliances, etc. as incentive!)

Sounds good, will look at 1031 exchange.

Couple years back I did give my long term tenants a $25 Walmart gift card.Its a tax write-off but more a gesture of good will @ the time because they were really good tenants.

Can you, this couple, their "next of kin", case workers (if any), an elder care attorney, all get together and allow you to do some type of compassionate "life estate" transaction, in the name of "good will" and at the same time, a "sound real estate investment" on your part?

I also think there are many out of state private lending opportunities that are good. Will