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Ask the owners of the league what they want to do once you fill out the league. That way you won't have a bunch of owners mad with your decision since they'll have the chance to voice their opinion.
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I disagree, unless you're conducting an initial draft. If you assign teams w/ players to owners, the owners who have aging veteran stars will want to play the 2003 season, and those whose teams stink but have youth will want to skip ahead. Then any decision you make will be seen as favoring one group or another.