Yes your last year of youth hockey (Bantam Major) is the year they should discuss the several options, and their advantages and disadvantages. Sadly very very few do just that. Good luck.
U14 is a **** show, be prepared for that and don't get discouraged and don't listen to all the talk from other parents.
Be prepared to do what is right for him at U15 and not what everyone else is telling you. Don't be the parent that shows up at the first u15 practice to find out that all the better kids are not there and they filled the team with anyone.
I know its tough to beleive listening to wacko parents but it really is a natural path, teams will start to ask for him, the better tourney teams will start to ask for him and things kind of fall into place.
With any luck he finds himself with a decent half season program, a good high school program, a good personal trainer and a good skills guy, in addition to him still wanting to shoot pucks or stick handle in the driveway or basement and this will progress fine.
Or he finds himself with a good full season program or academy that provides all that.
You cant prepare for the outside things, like him finding girls and wanting to hang out with them instead of training or working out. If he is truly passionate he will balance it or tell the chicks that he has to work out or practice.