Depending on the year and condition, I've seen CJ-5's around here go anywhere from $1500-$8000, with $3500 being about average. Insurance on my '75 runs right at $18 a month (with all sorts of discounts).
I've got mine through State Farm - it's liability only, no glass/theft/towing/comprehensive/etc. I also have safe driver, married, and firefighter discounts, coupled with carrying the other two rides and the house with them.
I've got a 77 CJ-5 that I paid $4750 for. Fiberglass body and lots of goodies. I am 20, have had two minor accidents involving only my vehicle and I've taken a driving course and my insurance through State Farm is about $130 a month. If you find a nice CJ that you like post its details on this board and we can give you a better idea on how much it may be worth.
I forgot to say that I am paying for full coverage. I thought about just liability, but since I'm still paying it off and will have it parked in a public lot 9 months out of the year I wanted the coverage. The way I saw it was that if something were to happen like it was in a major wreck I would still be paying it off to the bank even though I wouldn't have it anymore. Didn't seem to make much sense to me.
Ya talkin bout getting a CJ-5 for along side of your wrangler. I love my 5, but i couldnt see selling a wrangler to drive the 5 around. especially if ya live any sort of distance from work. I'm looking for a cheap cherokee to get me to and from work reliably. The 5 would be a great compliment to the TJ, though.