Just got back from driving a V8 Overland. It was great! Some thoughts:
Some posters had mentioned the ride with the 20's was rough. Coming from a Type S Acura the ride was fantastic. Ride quality was great, although the roads weren't terrible where I drove it. The wife loved it, even in back, and she gets car sick very easily.
The super sunroof is a great touch too, but it got hot inside quickly on a 40 degree day. Hopefully the motorized shade is durable.
Nav/electronics are great, except for heated/vented seat controls. That will take some patience and dexterity without a passenger on board. Didn't get to play with all of the screen functions but the salesman took me through the highlights and it is really cool.
The Hemi is great. I didn't hammer it but even in Eco it was peppy. I was going to try to hold out for the CRD but I may be swayed.
You have to be a total masochist to want the light beige interior. The GC I drove arrived with shipping damage inside; it was totally demolished. The beige shows EVERYTHING. Every scrape, nick, bump, speck of dirt and dust. Not good, black or indigo for sure.
Summer really can't get here fast enough.