This thread is great on it's own... also great at tying in some other important common dialog here on this site.
How do we best guide our kids earlier on to do well when they get to this point? How and when do we know to let go with each type of issue they face? We should work backwards a bit...
Middle school years - He wants to make the HS team? He wants to play travel ball? How much do we need to guide the process? How much do we let him take over? How much do we allow for deviation of chore responsibility with all this travel? How much is OK to spend on this crazy sports environment? Does he really love it enough to consider this as something he will pursue in HS? Beyond? Lessons? Really? Will he do enough follow up drills/work to make it worth while? Should I need to push him? How does this fit with him developing as a well-rounded person? What will he want to pursue as a career? What type of things do we need to introduce him to so he can figure that all out? Too early?
HS years - How much do we need to guide the process? Isn't it time for him to take over? But he is still an early teen, he won't make the right decisions. How much do we allow for deviation of chore responsibility with all this travel, daily practice, homework, etc.? How much is OK to spend on this crazy sports environment? Does he really love it enough to play at the next level? Is he getting all the proper instruction, support he needs to succeed? What part of this should he be driving? Are we making sure things stay properly balanced? He seems to love to play but doesn't have the work ethic... do I need to push or does it all need to come from him. He's just a teenager. What are his career goals? How does that match up with his baseball goals? What is the recruiting process? How much of it should be driven by him? He's just a teenager, he won't be able to manage that. Why don't the coaches want to talk to us and only to him? Is he good enough to play in college? Wow, he's a junior already. What do you mean this is the key recruiting time for him?
Staying above the fog in this crazy mess is really important. How we stay grounded and parent our kids consistently as our kids and not as baseball players is really important. It sure as heck ain't easy and no one has all the answers. But if we stay grounded in our parenting principals, ours are the ones that are most likely to successfully push through that first year of college and into adulthood. That applies regardless of whether they continue to play baseball at that time.
To add: In hindsight, I would say that most mistakes we made were those times when we considered making exceptions to our parenting principals - when we "reasoned" that exceptions were in order to ease the craziness. Stay the course as a parent.
When do you "let go" with each type of issue? Three adult kids later, still couldn't tell ya. But I'm pretty sure the answer is always a little bit earlier than you'd like to and it will always come with some "look, no training wheels" falls and bruises.