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If you are struggling with assessing players then turn scouting off at first. Then, all ratings you see will be "true" ratings rather than a scout's view.
If scouting is on, then always go with your scouting director over OSA. OSA is basically as bad as it gets, whereas your scouting director (depending on how accurate scouting is and how good he is) will be more accurate.
To tell by looking if a player is good, the simplest way is to use the star rating. A 5-star player will be very good, a 1-star player probably not. You can also use the more detailed ratings such as contact, power, eye etc to see a bit more detail. For every rating, a higher number is better, so just plug in the players with the highest ratings at first and see how you go.
No idea about feeder/winter leagues, sorry.
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