This could go on forever, but here's a few things you should know. The Overland has every option available (except VES which was optional), whereas the Limited ones may vary in accessories, depending on how it was ordered. It can be equipped exactly like the Overland, but won't have the front tow hooks, Overland seats, and a few other minor cosmetic items.
The Overland comes with the 5.7 Hemi, whereas the Limited could have a 4.7. The 5.7's are easy to mod. (see my signature), and respond well, as long as you get rid of the stock exhaust manifold logs. Do a search. If you get a 5.7, you can do a search and find everything you'd ever want to know about modding them. On mine, without major engine teardown, I am up about 100 rwhp over the stock version. Some stuff ain't cheap though. If taken care of (maintenance done in a timely manner), they are very reliable. There are a few that have had valve seat issues, MDS lifter issues, and stalling issues, some of which can be attributed to poor maintenance, and others that are manufacturing related.
As when purchasing any "new to you" vehicle, you should check everything out with a fine tooth comb, paying particular attention to everything in the drivetrain and suspension......engine, transmission, transfer case, both differentials, driveshafts, brakes, tire wear patterns, steering. Also, make sure all the accessories, windows, mirrors, Nav/Radio Unit, etc. all work properly and there is a map disc in the unit. Also, make sure (if it's and REC unit) that the programming "joystick" works in all 8 directions.
Pay particular attention to the transmission shifting (slipping/harshness), drive/reverse, reverse/drive transitions, correct fluid level (and not burnt or black), etc.
As far as handling goes, just get SRT springs,sway bars and Bilstein shocks/struts and it'll be great. I did this on mine, with SRT lowering springs, and it handles like it's on rails. IMO, these things are really neat.....if you take care of the maintenance in a timely manner and stay ahead of any problems that may appear. If it's your daily driver, you'll know how it should work and immediately pick up on anything that is not working as it should. Good luck, and hope you find a good one.
06 GCO, Dk Khaki, QDII, Flshing Hi 3rd Bk Lt, MDS "ON" Lt, Airtab Vortex Gens, Debadged, Fumoto Drain Valve, BT Catch Can, Chopped EGR Tube, SRT8 CAI, K&N Filter, Sonnax Trans Line Press Booster, SC Tuner W/Adv Trans Tune App, DS Tuner, Cust tubular hdrs w/3 in Magnaflow/Xlerator AP Exh Sys, Bilsteins, SRT Springs/Sways, Cust Eng Cvr, SRT8 frt/rear bumpers, FRI Sidewinder Cam/6.1 valvetrain, SLP 25% UD Pulley, BBK true 90mm T-Body, SOS Ign Coils w/.060 spark plug gaps, SRT Reps with 265/45&295/40X20's.