Getting a limited, you should end up with a full set of good stock Mopar skid plates, which I don't think are always included with Laredos. The Overland includes rock sliders, which are pretty slick, too.
I bought my '03 WJ Limited last January after having a '99 XJ. I lifted it 4" and put 32s on it, and it's great. I did a fair amount of research before buying, and would have gotten an Overland if I could find one that wasn't beat up. Still love my Limited though, and having gone from a peppy 4.0 I6 in the smaller XJ to a powerful 4.7 V8 (non-High Output) I am very glad I got the V8. I just can't imagine the 6 having enough grunt to give you a lot of confidence offroad. The torque is real nice to have.
On my old Cherokee, I went from 28" tires to 31" tires on stock gearing, and it was quite a lot slower. On my Grand Cherokee, I went an inch bigger with my tires, and the V8 has enough grunt that I don't feel the need to regear. If anything, I may get a chip, cold air intake, and exhaust down the road, but I still get a grin when I put my boot in it. Really, there's no downside to the v8.
I will say that mine came with a detailed carfax which says it was in the dealer a lot for the HVAC system, and when I bought it at 125k, it was still not operating right. It works well enough for me (it's a weekend warrior), but it does suck that it's not how it could be. I would prefer a simple HVAC system, but that's really my ONLY complaint. I love my WJ. It's very comfortable, very affordable when compared to other similar SUVs (4runner), and the solid front axle is awesome when you need articulation.
Whichever engine you get, I STRONGLY recommend replacing the rear sway bar as one of the first things you do. The front is pretty stout, but the rear is so puny it may as well not even be there. It leads to some unsettling tail wag, which I felt I was always overcorrecting for on the freeway. I installed an Addco 1" rear swaybar and greasable mounts/bushings, and the difference is night and day. Even with the lift, it feels very stable and planted.
Note the difference in stock vs. Addco swaybar:
Here it is stock:
4" lift and 32" tires:
