First, I would say look for the possibilities to make the boarding school work as best as possible.
What can you do directly? Have you considered actually boarding at your current school? Is that financially doable? If it's really an issue of coming home late every day, are there any activities that go late on some days, so that you have some long days, and then some short days? How can you adjust your schedule to make things work? You're going on 16, aren't you? Are you going to get a car for that commute? That might make life easier. On activities, have you looked at them all? You're young. Try things. Art. Music. Dance.
( I really can't recommend Dance strongly enough as something to get into young. It's fitness that can last and be used a lifetime. And it's a gold mine for young men, as there are a dozen girls trained in dance for every guy. I took up social dance after grad school. I'm 50 now, and dancing with girls half my age because I can. Me and my friends were just young morons for turning up our noses at dance. This falls under "try things" too. I had no idea I'd enjoy dance so much, or of all the benefits it would bring.)
After you look at your options for what you can do, I'd go talk to administrators at your school to see if they can help. Tell them you love the place - you LOVE the place - but you have issues because of being off campus and the on campus requirements keeping you from home. Could they reduce the participation requirements? Could they help further financially to get you boarding on campus? Maybe part time? What kind of high school doesn't have a math team?
Private boarding schools should have a good deal of flexibility in what they can do financially. Particularly with room and board, I expect that's just adding you to fix costs that the school already incurs.
I got a similar scholarship to a private (but not boarding) school. Though smart, I was not always so good a student. They counseled me and worked with me.
They want you to stay. They want you to succeed. They don't want you to bail.
Work for the best deal you can manage, and then decide.
The private school sounds like it would leave you better prepared, and certainly better credentialed to get into the best school you can.
The college you go to, and the friends you make there, have a huge effect on the rest of your life. I would expect the same principle applies to snooty boarding schools. You make connections that can last you decades. The college you go to matters if you want to go to grad school (because your grad school matters, particularly if you want to stay in academe).
The trade off you make now will be paying off in compounded interest for the rest of your life. It's a good time to suck it up a little for a long term gain.
I've noticed that when people tell me I have to do things, I enjoy them much, much less.
Everybody is like that. Particularly at work. Everything is a battle of status and control. It's not helpful. Try to let it go.
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I will now explain some practical techniques that I would give someone in your position. It looks like you have already implemented some of them. FYI I haven’t provided much background on any of the techniques, so if you want any more information on any of the mentioned techniques check out my post on the CFAR material as well.
Value Awareness
Prediction Accuracy
Agency
It can often be good to spend most of your effort on thinking about how to fix existing problems rather than moving to a whole new situation. It is common for people to not think about or to underestimate the costs involved with change. In your case, example costs would be having to get to know the new teachers and students in the public school. An example of fixing a problem could be seeing if it is possible to set up a math club at your private school.
This is so thorough! Thank you so much! I think my desire to transfer does spike when I feel lonely... a useful piece of information. :)