Speaking as a 'neighbor'(WY), we started looking at the X(base) and worked our way up to the OR. We've had several Jeeps and wanted the off road capability, but with some creature comforts and strong highway performance(which the Wranglers lacked). The OR fit these wants/needs and more.

IMO, and my wife's, the $3,000 or so extra we paid is well worth it. We haven't found ourselves wishing we had this feature or that. Much cheaper in the long run to already have the OR features than to try and add them. Plus they are covered by the factory warranty. That warranty was a big plus(peace of mind) with our Rubicon.

From our experience of trading in a lot of vehicles, you get more money back trading in a higher level package(e.g. OR vs. S) than you do trading in a lower level with a lot of add ons that you have installed. You'd like to think that features you have added have made your vehicle just as valuable as if they came on the vehicle, but generally that's not the case when it comes to the bottom line you are given for your trade.

So get most of what you want from the start and enjoy it. You're always going to lose money(depreciation), but, unless you like to 'build your own', you are better off starting out with all the available features you want.