I'm sure this has been brought up before, but I am just curious. For me, I was between my 2020 TH and a 2018 JKU Golden Eagle.
The biggest factor for me was price. I got the TH for about 28k, and the JKU was at 34k. I had a Mercedes E63 AMG at the time that was in need of a full head bolt and valve bucket replacement. It was my daily driver, and while I felt I could do all the head work, I would need more than just a weekend to do it, so I knew I had to trade it in and eat quite a bit of negative equity (about 4k worth). So going with the cheaper TH was clearly the better option there. Had I not been underwater on the AMG, it would have been a closer decision.
Towing was the next big factor. Long story short, I was being medically retired from the Navy, and it kind of popped up out of nowhere. Normally the DOD will pay for a move, but with the surprise medical retirement coming up, and my lease in Virginia ending before they said they would be able to move me, I knew I would have to pull my household goods behind whatever I traded the AMG in for. With the TH towing at 4500, and the JKU at 2000, the TH would likely tow most of my household goods. To tow with the JKU I would need a much smaller U-Haul trailer, so I would have to lose at least half of my household goods.
Interior was another big factor. The 2018 JKU if anyone knows, has a very spartan and bland interior. It was obvious the TH had the upper hand on this one. The TH kept the majority of the things I was used to in the AMG, just missing out on some of the minor options such as adaptive cruise, automatic high beams, and automatic rain detecting wipers.
Obviously with the Cherokee being closer to a crossover than a SUV, it rode closer to what I was used to. In just the short test drive in the JKU, my back really felt the rough ride quality, so that would have been a real stretch to try and live with the JKU (maybe the JLU is better in this regard, but way out of my price range) . I'm sure I would get some health care to take care of my bodily aches and pains eventually, but driving the JKU from Virginia to Michigan even if I didn't have a trailer behind me would hurt.
Now obviously I wanted the Wrangler for its superior off road performance and HUGE aftermarket support, which is why I went with a Trailhawk. Still decent enough off-road with a decent enough aftermarket presence. But sacrificing all of the above points just for that isn't worth it to me, especially with 95% of my driving would be on paved roads. Gladiator was on the top of my list, but to check off most of my boxes, I would need an overland or Rubicon trim, and that's just way too far off my price range at the moment.
So what about you? What made you choose your Cherokee?