08 Overland here.
Love the truck. We bought it with 30k miles on it a few years ago, sitting at 65k now. I bought the RRO lift (& 1.5" spacers, 265/65 Open Country ATIIs, Exhuast, LED Tails) about 2 weeks after I bought the truck...since it's a spacer lift the ride hasn't really changed at all, but I have since put 35k~ miles on it. I like the Commander because it is semi-capable in stock form, has big power despite not a huge footprint and love the boxy 'old school Jeep' look. The interior is nice-ish...typical and generic Jeep/Chrysler parts bin stuff, but functional and rugged. The Commander is not a big truck, comparable to the 100 series in the pic below. It's not a huge amount bigger then a Grand...so keep that in mind. I wouldn't buy it solely on the availability of having a 3rd row seat.
I actually just got back from a Colorado trip where we were 'trapped' in a blizzard near Clovis, NM. We were stuck in the truck for about 12 hours before pressing on by climbing over the median wind the winds died down. The Nation Guard was pulling people out of cars that had died, and apparently there were 60-70mph sustained winds for over 8 hours. Absolute zero visibility. Luckily we knew what we were driving in to and us along with our other party were massively prepared. Other than being bored, no prob! We had zero trouble with it and it never slipped or acted like it was going to let us down. For the record, the truck was RUNNING from 8am on a Sunday morning until about 8pm on Monday only turning off for the few gas stops and 2 lunch stops on the 600m trip.
It drives much bigger than it is and feels 100% solid on trails. QDII is one of the best traction systems you can have a 4x4. I'd love to put the Superlift on it and crazy with baskets and wheels/tires but my wife has already hit the garage once as it sits...lol. It's a great truck and we are thrilled with it. With these mods + the 5.7 expect 12-14 mpg all the time.