If he's a good player with talent and loves to play the game it will work out if you don't get in the way! This is the age where I stopped coaching my son.
-I am not big on weight lifting until HS. My son didn't lift until the end of his freshman year for football.
-I might add the outfield position is not heavily recruited in most D1 colleges, so if your son has any interest in other positions I'd encourage it. The right fielder on my son's college team played SS in HS, my son a catcher platooned in LF with a 1st baseman and 3rd baseman. The CF was a legit CF in HS but was wicked fast and got great jumps on balls.
Many have said it, its really up to your son to achieve. The amount of parental pressure to practice, get better, etc is usually inversly related to actual improvement and love of game. I would also be concerned about making baseball too clinical at this age. A lot of kids lose interest in this age group so I think the first priorty is to play, rather then attend alot of clinics, trainings etc.. Results will vary greatly by player.
When my son was that age, the two kids that played in college both spent a lot of their own time at the baseball field signing up for opportunites to play for teams short of players and actually practicing with teams other then their own! Coaches love kids that show up for thier practice and it leads to other opportunities from people other then the kids parents. You can't be afraid to let him hang out at the field or work out with kids that aren't on "his" team. If your son is really good, he can even learn from bad coaches
As an aside there aren't many guys playing the in Minor Leagues waiting for a coach, agent or parent to tell them what to do next, pitchers excluded
Good luck