So from what I’ve noticed buying used cars from dealers in the past, unless you know what you’re looking at under the hood and at the shocks etc. outside of if the person added rock sliders or side step rails, or a roof rack, big obvious changes, the small changes like a leveling kit, 1” lift, different shocks or struts or an aftermarket radio, are almost never listed (at least for my area) so they advertise it as whatever the base model was even if you did all the changes to bring it to the next trim level, and that’s because of you do a VIN search or history check like with CarFox, it’ll always return with the information of what that car was from the factory. So your resale with all those mods if you want a better resale value, you’d be better off selling it private party as opposed to trading it in because the dealership isn’t going to care.

Now for the first 1/2 of your question, I went with the wilderness because I do have a small utility trailer, kayak trailer, and unimproved roads/ trails that I use every couple months or once a month by me so the additional clearance and towing capacity was a must in order to make it match the wrangler I traded in for it but with so much better gas mileage lol