I used to lease (call me young and stupid) but was cognizant to never get out with any negative equity. Chose the JLU because I missed the JKU I had and think it’ll age well (asides from the other fun/expensive factor of mods ). That’s a good plan of attack; may try to grab a sports car at some point so I have the best of both worlds?I wouldnt waste my time, either buy the new one or live with and enjoy your current Jeep. My strategy is never trade, add to the fleet and use the oldest ones as winter beaters. This way you cheat the depreciation lock in when you trade, you get multiple vehicles to drive all year, it is like getting a new car every few months I just swap insurance onto the ones I am driving and park the others under car covers, allows me to do agressive maintenance and detailing so they all look brand new.
When they get 15+ yrs old, and 200K+ miles I retire them. Sold my 03 PT GT when I got my Rubicon last year, still looked pretty good considering it went thru 16 Maine winters, most imports are toast up here in about 10, I rust proofed it and it only had on small bubble on lower rocker, rest of the car was solid.