The new way of leveling makes it very easy to catch up to everyone to endgame, however, this is a great thing for all people coming back to the game, for people completely new I still think FFXI is really not as enjoyable. Depends on what kind of gamer he is. If he enjoys putting all the attention on the endgame, gear farming etc, then sure go ahead, however, all of the rest has kinda disappeared.
I would highly suggest doing at least the missions each at the corresponding level, if anything to experience that part of the fun we had back then, because going at 99 and oneshotting X boss is really not as inspiring. And also I would encourage exploration, I loved running around discovering new places when I was a low level newbie.
I agree with this. One of my most fun and recent experiences was leveling my Elvaan Rdm on Bismarck, and when I got to level 50 I soloed CoP up till Chapter 3. Then I leveled up to level 64, so that I would have erase from Whm sub and continued to go through COP.
The 4-2 Ouryu fight is insanely fun to solo as a level 64RDM/32WHM. It was also challenging. It took me, a 9 year FFXI veteran, 2 tries. I would also say that it's not possible for any other job at that level.