I think once you get to HS you don't need to do winter training with the travel team. It is high school time. The school will train as a team and instead of going to that second team practice, work on your own time (lessons, cages once a week, throwing, etc). Leave the travel ball in the summer/fall
On that note, if you are paying for an academy team you need to have free access to that facility 7 days a week. That's part of the inflated cost of playing for the academy - you don't have to pay for winter training/cages because it is already included in the cost. They don't have the rent the facility so they shouldn't be charging extra.
As for the coaching, once you get into the HS travel scene, there should be a reasonable expectation that every coach is experienced/qualified. Daddy ball ends in HS. Sure some are better than others and have more connections, but they're almost all good (or at least experienced) coaches as you start moving up the ladder.
If you think this program is the right fit and see them getting your son to where he needs to be as far as recruitment/development then you are in a fine spot if you're ok with the price tag.