This is a great thread from two basic points.
First off, there have been over 30 replies in just as many hours since the original post- this is amazing as to how many people read and participate on this forum.
Second, with all the posts, no one has hijacked it, or engaged in serious trash talking nonsense which again still shows this thread has some promise in truly being helpful. Thanks everyone for being so helpful to the original question.
Now, for my two cents, which will hopefully not violate the second point. If you are looking for a Jeep JK, (sport or Rubicon) either will treat you well right off the lot. So just go for what you can afford and what you want. Most people buying a car will think ahead "What will I be using this for", If your situation is daily driver, out on forest roads, driving on primitive roads for hiking/biking/camping trails, then the Sport will do just great. 4-Wheel drive and a two speed transfer case will do wonders with the stock tire and wheel clearance. If you decide to get rid of it, fine, just trade it in for the higher 4% value as stated in an earlier post.
Now, let's say you become a Jeep junkie like me and about 1,000,000 other people on this forum, and get the itch to go 4-wheeling or further out into nowhere. No problem, the aftermarket support is phenomenal for the Jeep and you can evolve into "Your Jeep Version 2.0" by adding maybe a rear locker and a winch, maybe some sway bar disconnects. This will give you even more confidence to go where you want. If you fall out of favor with off-roading, no big deal, it's not like you are invested too far into your rig, and the next guy/gal will pick up where you left off when you sell it.
If you are confident and know for a fact you want to "go nuts" into the great sport of off-roading, then the Rubicon will be a great place to start. Factory lockers front and rear with electronic sway bar disconnects and a lower geared transfer case will give you a great place to start, and you can readily invest in a winch or other important recovery aids. If you don't want these features or don't think you need them, why buy them? There are plenty of used Rubicons out there where the locker or sway bar switch has never been turned on at all. If all you want is the Rubicon glitz, why not buy a Sport and just get the Rubicon decal and glue it to your hood?
(BTW, I agree with an earlier post that lift and tires for better ground clearance, (not just looks) will be important for Sport or Rubicon, but not essential up front since the ground clearance is great already)
Technology and engineering in four-wheeling is essential, but as with all motorsports, the skill of the driver has to be present to do what you want your Jeep to do. One can certainly compensate for the other to varying degrees. We all know of people who can take on serious trails in a stock Sport while a new guy in a Rubicon holds up the group getting stuck all the time. Ultimately, there will be trails that both are required, but only serious off-roaders drive on them, and for these drivers, they already know what they want in a rig and have the moxie to make it work. One could argue a perfect world would be an experienced/skilled driver in a Rubicon (or other Jeep with a lo-gear transfer case, lockers, and sway bar disconnects) to take on some of the toughest trails, i.e. the Rubicon itself, but that is just an extrapolation, not argumentative.
In the end, I feel the classic adage is, "We all started from somewhere, so just simply start and see where your Jeep takes you (literally)."
Now the next thread will be "How one can start a local Jeepers Anonymous support group", members will find therapy/support because they have difficulty staying on paved roads and an overzealous desire to add random mechanical and cosmetic upgrades to a perfectly normal vehicle.
-skjeeper