im in kinda the same boat ure in. im debating on either lift it, or work with it stock.
skill is definately a factor, knowing ure limits, how to place wheels, etc...
i was looking at a 4wheeldrive mag one time, and it had an article about steps to modding ure stock rig.
to have a competent trail rig, a lift is not necessarily the way to go. sure u can fit bigger rubber and it looks better, but it also raises the center of gravity.
start with bigger tires. i believe the biggest a stock xj can fit is 235/75 series. try some bfg at's or swampers (depending on ure highway travel)
the next big mod are lockers. sure some people dont want drop 400-500 bucks on parts they cant even see, but the results are great.
add a winch/winch bumper. even the biggest rigs with the baddest tires get stuck and they mostly resort to a winch. its just about as good as trail insurance.
and with ure xj, def add some sway bar disco's...they'll raise the suspension felx travel to help u get over obstacles better. aftermarket shocks will not only give a better ride quality, but most are longer than stock. shocks are often a limiting factor in how much flex u have, so having them longer = more flex.
with all of these, u have an awesome base platform for a trail rig, u keep basically good mpg, and the center of gravity is low, making it a bit safer on the trail and road. and should u want to add a lift, or 33's...all u have to do is add them.
/rant