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OK, all the know-it-alls are out. Let's go back tot he OP's question.
Every org is different. Some handle kids and families better than others. Some coaches have more pull than others. We don't know which org or coach the OP is referring to, whether they develop kids, whether they are good or bad.
So, the basics. If your kid is having fun, and if you feel he is being developed and challenged, if you have a good coach/asst. coach, if it's a good locker room, if coach's kids aren't being overtly advantaged in terms of playing time, and you'd like to stay, check in with the coach in January, just to make sure. If he says Johnny is definitely in his plans, ask him what his policy, what team's policy is in terms of providing contracts - when should you expect it by? If he says "after tryouts," you have to decide - do you trust him enough to wait?
But, always have a Plan B, too. Know who you would want to go to if something changes last minute, because sometimes it does. You don't make a team in tryouts. it's just the way it is.
When is the right time for the head coach to tell the team he is not coaching the team next year?
"Signing a contract", absolutely hilarious to read when talking about kids of this age....you folks are pretty funny I'll tell you that!
Thanks tips, I'm well aware of that.....and it's still funny! I think it's hilarious to watch all the dads act like Scott Boras during free agency.....
^^ Exactly - well said.