New Canadian Parent - Our Journey

Good morning,
I figured this is as good as a place as any to mark our journey. Over the last couple of years we had a coach come up to Ottawa and answer questions about US boarding school. My son was really excited about the notion of attending a boarding school for football. At the time we said no (he was in grade 7), but as time moved on it was more apparent that we would change our minds. My son put all of his free time into training and maintained an A-/B+ average.

 Now 14 my wife and I started discussing boarding school.  My wife at the time wasnt prepared to let our 15 year old son attend boarding school in the US; as we live in Ottawa Canada.  We then decided - were we going to stop him from his dream to play NCAA football. Plus with his desire to be an International Lawyer he would be better off in the USA.  

 Our reasons for choosing this path were twofold.  One to get our son a great education - we read about the small class size (helps with his ADD).  Finally, for his development and exposure to football.  Off we went into the prep school applications and planning.  On Dec 9 we decided to start looking at enrolling our son into a boarding school.  

 We spoke with a scouting coach (bad move $$$) he had us apply at 3 schools Mercyhurst prep, Choate (well had already set this up) and Taft - we also applied to St James in Maryland. My son scored a 1986 on his SSAT which was good for a full time French student.  Well unfortunately we were declined by Choate and Taft.  

 Well on March 9 we received an acceptance email from St James Maryland.  My son is very excited.  I know it isn't as prestigious as other schools, but we left registration to last minute and listened to a thief of a scouting company.  

 I have a few questions now.  
  1. If he is at a boarding school is he considered out of state for college application (Canadian residence)?
  2. Is it considered bad to transfer out of a school if he doesnt like it (sports, people what have you)?
  3. This is his one shot at a scholarship (yes we know the odds) should we be looking at bigger schools?
  4. Do you have any regrets (for those of you that have sent your kids)?
  1. No. You don't pay taxes there.
  2. No, but you should not go into it with a plan to transfer. While there are reasons that students transfer, most schools and students assume they will be there for 4 years. I do know several kids who did a PG year (after 4 years of BS) at a school with a bigger football program as part of their recruitment arrangement. It is much easier to play on a big, top football team at a large regional public high school in Ohio than it is at prep school. There are, of course, some privates -many Cstholic) that are football powerhouses (Don Bosco, Mater Dei, Central Catholic ) but most aren't BS.
  3. If this works for you financially and is a school you like, there is a lot of risk in trying to optimize. A bird in the hand is worth 2 in the bush!
  4. I love the person my son became and the education he got at BS. Can't imagine it having been any better any other way.