Linden,

will you be the mechanic or do you want him to learn to be one? Nelso makes a good point about cheaper and fixerupper if it teaches him a thing or 2. if it ends up you doing all the work, then saving $500 for a few weeks of work may or may not be worth it...

I've not owned a road trail, but the reputations of the older Hondas and Yammys is pretty good. Either way, a couple of grand is low enough for learning purposes and as Nelso says, learning the trade. +1 for Dale Corser. I took my son who was 16 at the time and did the course myself with him. We both learnt a few things and then I took him to a Bernie Hatton school as well (which I also did). that taught him a few things as well.. he was trail braking into corners on his L's course and his confidence in controlling the bike was obvious.

tuition, practice and tuition... regardless of brand of bike.... keep it lower CC - 4stroke <250, 2 stroke <125...do that for 2-3 years and things will fall into place..