Nix
Like Dagwood said, if HE is still into it, then I would say to enter him. We were at Ottawa at 37 last year in a 32 man bracket with about 25 or so kids. There were kids of all levels in the bracket. After about 2 rounds, things had sorted themselves out for the most part and I think that the majority of the matches were competitive from that point on, regardless of skill level. It is a good experience and if you make sure he sees the Parade before the Finals, it may help HIM contribute to setting his goals for next year. That is the way it went for us last year anyway. Good Luck!
On another note, I think I read on another post(unless I've confused you with someone else) that you are Chris Hernandez' cousin. I worked with Chris for awhile and still talk to him some. Look me up @ Ottawa....look forward to meeting you and your boy.