Simply put, yes. HW is pretty strict when it comes to letting students take time off, for any reason. I know for a fact that they do not allow students to pursue acting et c. professionally—one of my friends attempted to do it and it was an uphill battle—but I'm not sure how that would apply to sports. HW is very proud of the education they give their students, and anything getting in the way of that is an issue. That said, for someone who is recognized as being a gifted athlete / artist like JJ, they might make an exception. They did have an equestrian team, which was a way of allowing kids who rode semi-professionally to continue to do so while affiliated with the school (don't think that we all went to equestrian matches or anything, football and basketball were much bigger deals). Maybe they would start a figure-skating team just for him?
And don't forget the demanding academics. A lot of the kids at HW are academic superstars, and would be valedictorian at any other school. That's not to say that there weren't dunces, but kids at HW tended to be smarter and more mature than the average breed.
Thanks!
One last note—I noticed someone somewhere in the thread postulating that there would be a lot less bullying at HW. That is undoubtedly true. I don't know what it was like from 2000-2004 specifically, but while I was there, kids may have said "gay" or "faggot," but there was never any outright or tacit bullying of me as a gay teen. Everyone was extremely respectful to me as a human being, and any bulls**t bullying would simply not have been tolerated by the school.
Also, when Will gets to be a senior (2004) there will be a rather,ahem, interesting, event that takes place at semiformal after party. Ask me about it if we get there.