Well here is my take on XJ's and your dilemma...
Pro's to XJ:
The XJ has 4 letters on the front of it that say "J E E P"
You will look like a badass in it
You will be more inclined to have a beard, therefore be more manly
Has room for hauling guitars and making sweet rock fusion to the ears of mortals
Your kids will love you more
SeXJ
Solid axles with unlimited spare and aftermarket parts
Ride would be very nice with OME or bilstein's
They're a dime a dozen
4 doors are pretty roomy for the kids
Inline 6, very reliable
AW4, very reliable
The 97+'s are very nice. I've had 2 98's that had more creature comforts and amenities my 94 doesn't. 99 is the best year, IMO. Sorted out wiring issues, newer body style, interior, no 0331 head to worry about. The 0331 head came on 00-01 XJ's with a micro crack in between the 3/4 cylinders and is given a bad name for being a problematic issue. I've never seen or heard of them being an issue on a cooling system that was functioning properly. Should have probably been a recall, but Chrysler is cheap.
There are spare parts for these things literally everywhere.
Cons:
Lol
Pro's to the Yota:
I'm sure the they will have an even nicer interior
Bigger vehicle inside and out/ more room
Possibly better mpg?
Cons:
I would go out on a limb and say maintenance would probably be more expensive, especially if a part goes bad.
I'm not as well versed on yotas as Steven or Jason, so I'm sure my opinion doesn't seem like much there. Nothing against them, Jason hauled me around at Chocco
But some would probably say I'm "Biased".