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It's tryouts, not sure how you define shenanigans and treachery. I think the only folks that are surprised are the "newbies". Just remember these simple three rules:
1) Don't believe the coach when he tells you that your kid is okay but doesn't offer a contract. If you find yourself in this scenario, start having your kid skate with other teams. Maybe he is going to be okay but better to be safe than sorry. When he doesn't get the contract, you shouldn't be surprised. (Yes, it's happened to my kid.)
2) Most organizations are not loyal, especially if the team isn't winning. If you don't have a contract in February, you need to be skating with other teams. See rule #1 but also remember, chances are the organization owner barely knows your kid. He doesn't care if you are easy going, you pay on time, etc. He just knows the team isn't doing well and that's bad for business.
3) Tryouts are a money maker for organizations. For most, the core of the team is set well ahead of tryouts so you are now among a large pool of kids trying out for the few remaining slots. There are so many variables that can affect how your kid does in a tryout, your chances of making team are increased exponentially if you skated with the team before hand.
Now with my "preaching" from the mountain top out of the way, I do know someone who had his kid skating with an elite team for a number of practices. The coach told him to bring him to tryouts, that he really liked how he looked but doesn't offer early contracts. Night one of tryouts he's talking to one of the parents on the elite team and learned the entire team had been filled prior to tryouts and later confirmed that evening with the coach. Not sure, does this qualify?