I've had a Jeep for about 2 years now. I took it out on some easy trails a few times and had fun (Dakan Road, Devil's Canyon) and had fun but wasn't really too obsessed.
Then this year my brother took a month to do the Trans America trail and stopped here along the way. I went out with him and he pushed me more than I had been willing to go before and I have been a lot more adventurous since.
I enjoy trails with a little challenge and great scenery. The last couple of weeks I did Middle St. Vrain/Coney Flats up in Boulder and Argentine Pass in Georgetown and had a blast with those. Coney Flats is about as crazy as I'd like to get and also what made me think "hey, I should probably not do this by myself"
The Jeep is still how it was when my parents bought it used in 2012 (Bald tires and all) apart from new transfer case linkage I put in so I could get it into 4 Low.
I'm actually getting new tires tomorrow - 33" Toyo Open Country M/T so that I can do more things and not be a liability to anyone I go out with.
It already has a 2" body lift and I plan on getting the OME 2" lift in the very near future.
Looking forward to meeting people who know what they're doing!