You need to do some reading over on
http://www.jeepsunlimited.com
First of all, you do not need a rubicon.
Second of all, as far as pricing goes, make sure you check out
www.jeepwarehouse.com to get an actual idea of what the models should REALLY cost you. (dealers will mark them up ridiculously)
Third of all - I have a wrangler, and it's an awesome vehicle. HOWEVER, it is a great SECOND car. It is a lousy ONLY car. If the wrangler is your only vehicle, you'll hate driving on the interstate, you'll hate going shopping, you'll hate trying to fit your stuff in it, hate driving in the rain... it is really one of the least practical vehicles you could own... but most people who own them think they are fantastic.
The only real requirement when buying is that you should buy the 4.0 liter 6 cyl model. Other than that, the X is a good value, the sport will have most of what you want. There is NO reason to buy a Rubicon unless you are a hard core offroader - it has $2500 worth of extra offroad additions that will do you no good whatsoever on the road. A stock wrangler is already very capable offroad, so no reason to go overboard.
There is no reason to buy a hard top wrangler. That's just senseless, since the convertible aspect is really what makes the wrangler great. The soft tops take a bit of work (5 mins) to put up and down but when it's down it's the best convertible you'll find.
PS: They are virtually unchanged from 1998-2003, so don't be afraid to look into used 4.0 wranglers.
PPS: They aren't big. Don't ask me how it works out, you'd think a big square box on wheels would have lots of interior space, but there's barely room for a duffel bag behind the rear seat, and 4 people can only fit VERY uncomfortably)