Hey Root, sounds fun.
Son was assigned to a team in this league a few years ago, along with three or four of his D2 teammates. We did some league research and most teams have solid history and decent following. Not one of the top leagues as far as high level players but strong enough that he'll get a good dip in the water. Ultimately, son and his teammates (and their college coach) had issues because costs kept rising from the time they signed contracts so they eventually backed out. But this was isolated with this team and the team is no longer in the league.
Jamestown doesn't get huge crowds but several of the other teams in the league draw 1K plus. Mostly rural upstate NY towns. Jamestown is the geographic outlier and some of those bus rides will be on the long side. NY lakes region in the summer for a month or so doesn't suck. Half a season there sounds like an ideal intro to college summer ball. Do be aware of costs, however. The league seemed to be on the high side relative to other summer college leagues. For us, though, the kid would cost us more staying at home just with the increased grocery bill.
I think the important thing is to clarify and double check what role will be and what the plan would be for innings. That expense, time commitment and travel would be a shame if he ended up with virtually no innings or was put in harm's way with lack of rest between appearances.