I recently went through the same dilemma with BMW/Jeep. I drove BMWs for the last 12 years. I had a '99 328i, '06 328i, '08 X3 and lastly an '11 528i.
I wanted an SUV and I looked at the new X3s (I don't need a guzzling X5 and the wife liked the X3). My biggest issue was that after 12 years, it felt like the same damn car every time. It didn't feel like I had something new. Just the new car scent and the same damn interior. Very little changed.
I looked at the JGC, Audi, X3, Tahoe, Acadia and even the Buick SUVs.
In the end, I took my 528i to CarMax, got a great deal and my dealer picked me up at the CarMax so I could hop into my new '14 Overland. Just pulled the trigger 2 weeks ago.
-More features than my BMW had.
-My monthly payment dropped $100/mo (even with extra warranty to cover 15k/yr miles on the lease).
-My insurance dropped $600/year.
-Navigation is amazing compared to the BMW crappy system. Horrible routing too!
-Touch screen compared to that annoying wheel to enter data.
-The '14 JGC actually has a very smooth ride, for 20" wheels.
-I can actually get our kid's stroller in the back (528i trunk was big, opening was not).
-I can see the road ahead of me, past other cars since I'm not sitting 12" above the street.
The dealership experience is VASTLY different and that will take a little getting used to. You're pampered at most BMW shops but I've built up a good rapport with the Svc dept at my dealer and they're pretty cool with me. Plus I like that i can go to the Goodyear shop 2 blocks from my office for maintenance as an option.
So far I'm VERY happy with my vehicle and I'm looking forward to the next 3 years. If I've had no major issue, I'll most likely get another one.
2014 JGC Overland
V6 & Stebel Air Horn in True Blue / Vesuvio Blue/Brown.
What pays for my Jeep: IT Manager / Network Engineer
Prev: '90 NSX, '96 3000GT VR4, '99 325i, '02 ES300, '06 328i, '08 X3, '11 528i