I don't think you're going to like a lot of what I have to say here, but....
* Why are we talking about a 14U training all winter? What about playing basketball? Soccer? Football? The side benefits of cross training by playing other things are far more than folks give them credit for. Having coached a lot of kids and parented two college and pro players, the biggest leaps any of them took was when they played another sport at age 12-16. And you should think about whether this extra training is driven by your son - or by you? I have to tell you, I know many, many college and pro players and I knew some of them at age 14, as well as some who didn't make it - virtually none of them was self-workout-driven at that age. In fact, I cannot think of any - and my list would include current MLB players.
Let kids be kids - age 14 is awfully young and there is plenty of time for intense training down the road. As a legendary college coach once told me, 'I worry about burning kids out with today's travel ball/workout culture.'
* Ask yourself - did you take your son off that team because he wasn't good enough? Or because he wasn't playing enough? Two different things. If the former, maybe not a bad decision if you see no way for your son to surpass the talent level of the leader. If the latter, I suggest you may(?) be giving your son an "out" rather than challenging him to step up his game to get on the field more.
* Ask yourself this too - is all the money it appears you're investing worth it? At this age? Academic money can often be more than athletic money. How are your son's academics? Have you even done a rough-order calculation about year-long training and playing in a different state costs vs. a possible (emphasis - POSSIBLE) 25-50% athletic scholarship? Cause thats what you're shooting for most likely.
I think you are likely to do what you want to do - but at some point you should ask yourself the questions above. They are good questions. If money is no issue, some of them go away.