I am on the pro Jeep side.  Nothing better than doors off, top off rolling down a paved road and taking a hard left on a dirt road and not being concerned with what obstacles may lie ahead.  Second best is doors and hard top installed, heater blowing somewhat warm air as you drive down a snow covered trail surrounded by trees.  
I made the unfortunate mistake of selling our 1999 TJ a few weeks ago and am still kicking myself.  I purchased this TJ in 2011 and most thought I over paid but seven years later I sold it for $200 dollars less than what I paid.  Not a bad investment:).  This TJ was a manual transmission and due to the DW medical issues it was no longer comfortable for her to drive.  
Overpriced or not I will definitely purchase another wrangler. The off road ability, the ease of towing them, the open air summer rides, the winter treks through the woods, the conversations and friendships with fellow jeepers, the amazing resale value, the ease of getting around congested downtowns, the feeling of driving a lifted covered wagon down the interstate and the waves from passing jeepers all justify the high price of admission for me.  
Now to start the search for the next wrangler to join the family:)