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I'm considering buying a Jeep. Advise and smart-a** comments requested

1998-2002 are the best ride coil springs not leaf springs still old school looking and have the 727 style automatic transmission only a 3 speed but best automatic for a jeep, 4.0 tried and true motor, the 2003-2006 4 speed transmission if you take extra care of it maybe 100k miles, and the 2005-2006 are known to have wiring issues. Don't know much about the newer models other than stay away from the Fiat owned Jeeps Dieselt Dieselt will vouch for that.
 
This guy has or had a pretty awesome rig for sale, it's marked as gone, but it may be he just pulled it from the market (I think that's what happened when I was looking heavily at doing a deal for it). https://www.theoutdoorstrader.com/threads/item-gone-ft-1989-jeep-wrangler.2943017/

I ended up with a 2 door 08 manual rubicon. I just kept checking cargurus for my price range and I eliminated everything with accident history on carfax. A four door is DEFINITELY a better overall investment for practical use, but the two door is shorter, nimbler, and just plain fun. I bargained away my rights to motorcycles when I got married, I've never owned a convertible, but now I have a weird hybrid of both and it scratches the itches with the doors off and top back.

The newer Jeeps with the pop-off hard panels are also much much better than soft tops, speaking as a guy with a soft top and a father-in-law with a hardtop 4 door. He uses his Jeep as a daily driver, mine is just for fun runs. My 08 Rubi is smoother and nimbler than his 19 sport, especially when we hit trails in North GA

If you aint in a hurry, keep your options open. Something will pop up that fits the bill.
 
You'll have fun in any Jeep you find for your price bracket. You'll find more things to buy for it after than you could imagine.

More than 2 adults and a kid I'd recommend a 4door. 2 kids 'could' fit in the back of a 2door but it's super tight.
The jk/jku and later 3.6l is way better than the anemic old 4.0. None of those are a v8 but way better than the other. Not aware of any specific things to avoid persay that's unique from any other used vehicle. Look for good maintenance, lower miles, etc.

Not all 4 doors or automatics are mall crawlers. From my last Moab trip.
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If I bought an older Jeep it would be a v8 swapped JL but the kids guidance still holds there. As far as SxS they are better offroad given the size/etc but I can drive to and from the trail on the highway in a Jeep and use it for the occasional grocery run. A lot of SxS are the same price as a Jeep as well.
 
Bought my wife a new Jeep grand cherokee L. She didn't care about the hemi but I did. After the first time she drove it on her own she came back and said, I'm glad I have the hemi! I really like the Jeep !
 

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