Hi Roger,
I just had the front off side malarky in bits on my 2002 WJ a week ago.
CV joint boot had a small hole in and CV was cracking only when steering hard over. It was ok in a straight line however been driving with an egg up me backside for two weeks for I thought the thing was going to explode any minute. When I did get it off the half shaft however it looked and felt like it was falling to bits in my hand despite still being full with grease.
As for the wheel bearing : they are a sealed unit so not servicable. It's either good or not and nothing you can do about it apart from changing it.
In my opinion a disintegrating CV would do more damage then the wheel bearing itself. I guess a bearing would slowly grind itself to bits up to a point where driving further is not possible but not life endangering.
As for spannering (and you're taking to the ex chairman of the Birty mechanically inept club......Bulldog is now in the hot seat
). With the right tools you can whip the hub off in 30 minutes. The only bastards are the three 12 point bolts at the back holding the hub on. (I destroyed 2 ringspanners there.).
A beefy 12 point socket set is your friend here + a decent extending bar. Also a 36mm socket for your hub nut which you have to torque up until you can give no more + a bit to fit the cotterpin.
Some great info on US Jeepforum + 2 educational vids on youtube. (I'll have a look for the links).
http://www.jeepforum.com/forum/f310/how-replace-axle-shaft-wheel-hub-bearing-assembly-w-pics-377208/Cheers & good luck.
ps. links are there now so you're good to go
Edit 2 : just reread your OP...... how did you change the CV boot without going through the above process anyway ??