02Crush
Way past gone
Out of respect for my friend I am taking this down now.
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Every team is different, so there is not going to be a "one size fits all" solution to your dilemma. I will tell you that in order to keep our better players happy we tried to elevate the level of competition we faced every year. We started as a C-team, moved up to low-B, high-B, low-A and finally to high-A. As you can see it has been a 5 year process, so it is not something that is going to happen overnight. It also helps if you have one or two SOLID pitchers who "buy into" the process and are willing to stick it out. I truly believe that this "development" plan is one of the keys to my DD's success. She was brought along slowly vs. being thrown into a situation she was not ready for. She has always been our #1 or #2 pitcher, so she gets plenty of circle time.
Most teams go through some player transition every season. As the head coach, you need to decide if it is going to be the top 1/4 of your roster leaving for better teams, or the bottom 1/4 of your roster being cut to make room for better players. As you "progress" up the TB food chain, the answer to that question changes.
However in our age group (02 and 01), no one wants to be patient. They expect instant results and if not they hop. I feel it is worse than kids of the 00, 99, 98 and 97 ages I have watched.