A: Depends on what you want from your Jeep.
The CJ5 is a fantastic vehicle, and it’s ridiculously inexpensive. The best years for that, again, depend on what you want. The 72-75s have a Dana 44 rear and a V8 option. The 76 and newer have a more robust chassis, but a smaller engine bay. The 77-79s had a boxed frame and disc brakes. Finding 76 and newer parts is still fairly easy to do. Earlier ones … well, you’ll do a lot of searching.
The CJ6 is a strange little Jeep. I wouldn’t get one unless you’re a collector. It’s, basically, a long wheelbase CJ5.
The CJ7 was a really robust replacement for the CJ5. I liked the longer doors on mine, and the hardtop & hard doors were useable. Getting a post 1982 one won’t get you the heavy-duty parts that came on the earlier rigs, but you’ll get wider axles, Dana 300 transfer case, and it’s not that difficult to find one that came with a Dana 44 rear end. I’d recommend the straight 6 over the V8; same torque, better MPG (although MPG isn’t the reason you buy a Jeep).
The CJ8 Scrambler is an absolutely kick-ass Jeep. It’s a long wheelbase CJ7. I can’t think of one single reason not to buy one. It’s my absolute favorite Jeep. Same rules apply when looking for a CJ7.
The YJ was the replacement for the CJ7. It was leaps and bounds beyond the CJ7 … but the square headlights really irked Jeep purists. The hood was also really, really long (which really lends itself well to a number of engine swaps). You’d want to get the straight 6, and you want a later year. The 91-92s had the fuel injected 4.0 HO motor without the ABS, 94s, I believe got the bigger knuckles, and the 95 had the galvanized tub. Of all of them, the 95 – last year – had the best of everything.
The TJ came out in 1997, and stuck around for 9 years. The biggest major departure for the TJ was the coil spring suspension, instead of the leaf springs the CJ and YJ had. It is a the best ride. The aftermarket is strong for the TJ. Get the straight 6, get the manual. In ’03 the Rubicon model came out, and in ‘04.5 the long wheelbase Unlimited came out (it’s not a TJ, it’s an LJ). Personally, I’d look into one of these; the longer wheelbase makes for a better ride, you’ve got some extra space, and they’re a good looking vehicle.
In 2007 Jeep came out with the JK, and it is – as of the time of this writing – the model that is currently available from your local new Jeep dealer. In addition to the traditional 2-door Wrangler, Jeep now offers a 4-door Unlimited model..
If you can get a new JK, get a new one. If not, the body style has remained mostly unchanged since 2007. There were minor trim changes over the years. The ’07 JK doesn’t have the tire pressure monitoring system that the ’08 and up models have. Many Jeepers disparage the 3.8 V6 that was introduced with the new model for no particularly good reason; it is absolutely as capable as the earlier 4.0 (ooooh, I’m going to hear it for THAT comment!). The engine came coupled with either a 4-speed automatic or 6-speed manual transmission, NV241 transfer case, and 4:10 gearing – although some did have the less- desirable 3:21 gearing. Rubicons came with the Dana 44 axles and virtually bulletproof NV241OR transfer case. I’m not a fan of the automatic, but some people like it.
In their infinite wisdom, Jeep came out with a 2WD version of the Wrangler. Why? No one knows; they didn’t sell well and disappeared ignominiously (at discounted prices) from dealer lots.
While the Rubicon is the be-all, end-all of the factory off-road machines, my experience is that if you’re not going to off-road the rig, it’s a waste of money; it’s very serious and not quite as “livable” as the other models. If you’re an occasional weekend trail rider, then go for the Sport or Sahara.
In 2009, Jeep added Hill Start Assist, which prevents rollback on hills when starting from a stop.
2011 brought the new-design Jeep steering wheel with exciting new buttons, as well as a new interior which has remained through the 2015 model year, with the exception of the dash-mounted speakers.
2012 brought a major driveline change; the new Pentastar V6 offers 285 horsepower and 260 lb-ft of torque, and it’s coupled to either a 5-speed shiftable automatic that even I like (and I’m not a fan of automatics), or the 6-speed manual.
2013 saw the introduction of an upgraded Rubicon in celebration of the 10th anniversary of the Rubicon, appropriately called the “Rubicon 10th Anniversary Edition” which sported a beautiful (and functional) hood, bumpers with removable end caps, and other niceties that showed other Jeepers that you weren’t afraid to spend $4K on factory upgrades to a factory upgraded Jeep that already had $4K in transfer case, axles and driveline upgrades.
2014 and 2015 both had minimal changes, some additional special packages like the X Games, Willys Wheels, Modern Warfare 3, Polar and Freedom editions, and Jeep continued offering the upgraded Rubicon 10th Anniversary package, calling it either the “Rubicon X” or the really questionable “Rubicon Hard Rock” edition.
In order, I’d recommend a brand new JK 4-Door, JK 2-Door, the LJ (Rubicon, Sport or Sahara), TJ (Rubicon), TJ, ’95 YJ, CJ8, or CJ7.
Don’t get a 4 cylinder. They’re not bad Jeeps, they’re just really underpowered and don’t have the stronger drivetrain of the 6s.
I’ve owned pretty much every single model (including the newer JK).