First Wrangler, is Sport a good starter?

Forgive my noobishness. I have a basic understanding of Jeeps, but no off road experience (Really want it though.) I just leased my first Jeep earlier this year, a 2014 *cough*Cherokee*cough*. I love the electronics and luxuries of it, but it's not quite what I want. Even with the upgraded 4x4 (and the fact it's a lease) I don't feel confident enough to take it on any trails, or even use it enroll in the 4x4 101 classes. It will be handy come winter time, though. What with my complex refusing to plow the parking lots.



I want a Wrangler. At first it would be my daily driver, but I want to use it to upgrade and learn about it. As such, I don't want to care if it gets scuffed up. I'm thinking of going cheap and getting the Sport or Sport S (Gotta have A/C) if I buy new in a couple years once my current lease is up.



Would I be gimping my off road capabilities by going with a Sport and slowly adding to it? If you got a Sport, what would some of the first mods be? I presume better tires would be my first upgrade, possibly lifting it?



My current Cherokee has satisfied my "I want to be the first owner!" desire in my life, so should I skip a new Wrangler and look for used? Aesthetically, I'm thinking a two door with half height doors would be most what I want to drive.