Lenders in the RE space aren't the healthiest right now in my opinion and need some stable wins on their balance sheets.

The IRS sets the rules, and they are available on their website:https://www.irs.gov/retirement-plans/plan-participant-employ...

Most of my wealth is in retirement savings, a taxable investment account, and my house.

It's really stupid but but most banks consider the following to be rural: over 5 acres, if it has an unimproved road to get to the house, if it has a barn or horse stables, if population of town is under 20,000 (population density varies by lender).

There's a few other things to think about too: 1 - Possible owner financing if he wants to still get a stream of income into retirement at an attractive rate compared to the rest of the market (win/win scenario, you don't need to come up with as much cash, and he makes a little $ on the %) 2 - Consider a post possession if he needs some time to move out but needs the cash up front for whatever reason 3 - Leave all the furniture/junk in the property and you'll handle clean up etc. 

Condo Karen is much worse than some former builder retired into a code enforcement role.

I would like to be on about a 10-15 year out from retiring so equity is probably the goal.

I get where y'all are coming from in terms of "be happy you've had a long, stable tenant," and yet I want to point out they have greatly benefited from being in the building this long as well.  

These people are clearly the victim of some brilliant guru who told them how to retire early/escape the rat race/be their own boss/etc, but forgot to mention the part about it being really tough, and like 95% of people (rough estimate just from my brief experience here on BP) fail. 

I visited the area and discovered it would be stable, affordable, and profitable.