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
I disagree, this is completely individual school related. it depends on the HS coaches, demands and program. They vary greatly.
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.
This I do agree with to some level, not free and not 7 day a week but some access and pretty liberal access for a winter fee. IMO opinion a structured winter training with the Academy team is far superior to the HS for about 500. That typically is twice a week for 1 hour or 1.5 hours.
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.
I don't know what part of PA you are from but I am very familiar with the Eastern part of the state and NJ. What the OP is quoting is slightly high but not out of line at all and not even close to the top of the market.