Finally made my move yesterday. I had gotten pretty frustrated over the weekend seeing the same old overpriced turds posted over and over again in Omaha and started checking other cities some more. So Monday night I'm looking at Des Moines Craigslist, and I find what appears to be a pretty nice privately owned Grand Cherokee that has Bellevue, NE listed in the location. It has exactly what I'm looking for, 6 cyl, cloth interior, and not black and they were asking $5850, right in my price range. Plus the transmission had already been rebuilt in it which is a huge plus. While it's not unusual to see vehicles advertised in multiple cities, it damn sure is to see one listed only in another city. Thought maybe I had missed it in the Omaha CL, but double-checked and it wasn't there.
Kind of a WTF moment for sure, but then I thought about what COchief had said about ****ups like that...it's probably someone older and confused about what exactly they were doing. I decided to let it sit for a couple days and see if anything changed, my thinking was they weren't likely going to get many, if any, calls for it seeing that they had it listed in the wrong city, and they may take any offers they get for it seriously and I could get it for an even better price.
So I watched the thing like a hawk, waiting to see if they realized their ****up and the ad disappeared and reappeared in Omaha. As of yesterday morning, nothing had changed. I decide it's time to make my move. I call the guy, arranged to meet him, and sure enough, it was an older retired guy. He was nice as hell, original owner, had every freaking service record going back to the first oil change. He had just put new brakes, tires and battery in it last fall. It had always been garaged, never abused. I took it for a ride and it ran & drove perfect. Only issues I could find were a few very minor cosmetic things. I did throw him the $5k offer on the spot, but after some thought he declined it. I decided that I wasn't going to let a few hundred bucks get between me and a one-owner creampuff, and we eventually settled on $5400.
Here's my new baby, I freaking love it.
Also, a big thank you to everyone who gave input in this thread. This place is better than Consumer Reports. Nearly everything that was mentioned I saw at one point or another.