Great thoughts! If you don't mind, I'll add our #6 from experience:
Freshman didn't make the JV team, although it was a close decision. The player will likely get tons of playing time, develop great relationships with his teammates/graduating class, and be competing at a level where he is likely very comfortable (or even a beast).
One important thing I have learned from these boards is that it really doesn't matter to college coaches how early you played JV/Varsity, etc., because there are just way too many factors to consider, such as the strength of the classes ahead of you. Another is that it's all about at-bats. We tend to get hung up on my kid is "playing up" when maybe he's getting one AB per game.
Great advice!