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This will be an issue for new teams, but I feel like this will mostly correct itself as all teams mature.
That being said, in season 2, I got lucky with good deals on significant upgrades at 3 positions just before the playoffs. I was a wildcard team, but got hot at the right time and won it all... with all 3 upgrades on my reserve roster waiting for the next year.
So naturally, I missed the playoffs with those upgrades... :-D
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