I would suggest a 4door over the 2door. I love the look of the 2 door, but drivability and interior space of the 4door always comes in handy. You mentioned back country hiking, camping, skiing. It's nice to throw the stuff inside out of the elements and even sleep in the back if needed. It will also drive more predictably in snow and loose gravel.
My vote is for new. The odds of finding the ideal wrangler equipped the way you want, well maintained, and reasonably priced are against you with a used one. At least if you get new, you know what you have. If you do go used, I'd suggest looking for one that doesn't have aftermarket items on it. Until you're familiar with the brands and equipment out there you're not going to know the difference between a quality lift, or something done on the cheap to get the look they're after.