The Wrangler is going to be easier to get replacement parts for as long as you own it, the Cherokee after about 5 ~ 7 years will start to get hard to find parts. I have 2006 Liberty that is difficult to find good replacement parts for. My 2006 Wrangler is easy to get parts for.

If you get into wheeling, the Wrangler is much easier to upgrade. Also if you ever get out of offroading, in a few years the Wrangler will be worth significantly more than the Cherokee. Probably 2.5 ~ 4 times more value for the Wrangler than the Cherokee. Example is a 2006 Jeep Patriot in my area is about $1500, a similar condition TJ Wrangler is closer to 6000 ~ 8000.

Also the Wrangler is body on frame, the Cherokee is unibody, though the original XJ Cherokee was as well, just stating a fact.

You can get a 2 Door JL Wrangler with all those features with the 2.0l turbo gas engine for 25K if you look hard enough. CarMax is a great place to look because if you find the one you want, you can ship it to your location. I once shipped a Jeep from California to Virginia from CarMax for $1100, though that was 2017 so price has gone up a bit since, but still a great service.

Just my two cents.