I have no idea if I'm doing this right, but my criteria are
a) All else being equal, I want to put him in the league in which his current rating is closest to 50. Click the "Ratings Relative to" dropdown on his player profile, and adjust the league to see how your scout thinks he stacks up to that league. Ideally I want to set guys up to be slightly above average, and then promote them when they perform well above average.
b) Put him on a team where he'll get the playing time you want him to. If you draft a SS, don't put him in direct competition for at bats with another SS whose development is a priority.
Monitor his performance after that. If he seems overmatched despite your scout's rating, he may need to move to a less challenging league.
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