Cabbagedad,
Thanks. It's been through some reading online that I've realized that we need to be starting to think about things now and not wait. The D2 swimming thing just kind of fell into our laps, and I am hoping my son doesn't think that baseball will be anything like that. And as a parent, even that "easy" process was stressful!
I have been involved on the board for the local rec league, and while I have not shared everything with my son, I have shared some of the ins and outs and behind the scenes, a lot of which have involved coaches and former coaches. Since it is such a small town, he's been able to encounter most of his coaches both as his coach and as an opposing coach, and in other contexts as well (dad of a friend, local businessman, etc). He really admired the HS coach during the season, but once he got into Legion he started to realize some of the HS coach's shortcomings. But he's a very coachable and respectful kid, and that's part of what coaches love about him. I worry more about myself and my husband -- we often need to bite our tongues and watch what we say around our son and let him develop his own opinions and ways of dealing with things.
I really do appreciate all the feedback here. It's confirming a lot of what I already thought (he's not D1) and has given me some direction. I've already shared some of it with my son ("The first thing I got asked was 'What's his GPA?;" LOL). Living in Alaska I find online communities can help when we feel disconnected.