@buuzn03, I had a similar epiphany during DS's final exams before Thanksgiving break. If he'd been at home for his first set of high school final exams, I would have reverted to an angst-ridden helicopter Mom, standing over his shoulder while he studied, nagging, nagging, nagging... Instead it was just a few cheery "Good luck! Do your best" texts, while he was on lockdown in his dorm studying. That alone was worth about half the tuition.
It looks like you may have a solution, but if it doesn't work out, don't feel self-conscious about needing a favor. We are about 90 minutes from CTKid's school, and if a kid had a predicament like that, it would be a no-brainer to help out. I would think the dean's office or parent coordinator would be able to hook you up with someone local.
The flip side is that at boarding schools (at least on the smaller side), we have seen so far that there really is a spot on a team (or rec team) for everyone. At a much bigger public or parochial school, many kids would never make a V or JV team, and therefore not be able to play a sport, whereas at boarding school, they can play many sports at the 3rds or rec level, and try new sports to which they'd never have access otherwise. You have to expect that at schools that draw from all over the country and beyond, whether it's with PGs or kids repeating earlier, there are going to be some very high level athletes and the athletic programs are going to capitalize. And as others have said, many, but not all, kids repeat for sports reasons. My older son is the much more promising athlete, but we didn't consider having him repeat, and he made his varsity team as a "true freshman" (though he says he's in the minority in his grade). My younger son may very well repeat 8th or 9th grade for other reasons (he'd have to repeat several times to catch up size-wise for his sport). I was just talking to a teacher today who mentioned that the new trend, as an alternative to a PGY, is R-11 -- public school for 9-11 and then prep school for 11-12.
I agree with @gardenstategal and would also add that people are different. Some kids are more inclined to have lots of interests and hobbies (multiple sports or instruments, for example) and generally be inclined to try new things, and others may have one or two true "passions" and be less inclined to branch out, or just have interests or hobbies that don't fall into the standard extracurricular categories. However, authenticity will come through whether you've played a sport since age 3 or just discovered a love of cooking.