My buddie and I have just been through this. We both have EB's. As we get older, quiet, smooth riding, reliable, air conditioned, etc. rigs become more desirable. I have the thought that we can make our EB pretty close to the newer Jeeps with regards to the aspecs above if we wanted to spend the money and time to do so. So we both decided deferently on this one. I am keeping the EB for obvious reasons. However, I am dropping it down a few inches, shaving some tire size down from the 40's, installed an Auto (bad ass auto though). With this I will rebuild my spare tub so that the doors shut and seal, paint will be nice shiny, stc. My plan is to take the eb back to the state where the wife and I can take it out on the weekends while still making it through the Con.
My buddie on the other hand is going to sideline the EB and build a Heep. He bought a 93 4.0L Auto. He is doing this for the above easons but building it a little overboard with a 10.25 rear, Dana 60 front ARB's, Atlas, and Staz's beadlocks on 40" Goodyear MTRs. He is going extreme for some, light for others but one thing is true it will be a wheeling rig like mine, a bit more comfy, a little quiter on the freeway....this is fine but it is still a bought rig and not really built.
I'll stick with my EB.