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Yes, to have the "full effect" you need to run it after each season, before clicking the 'Proceed to Next Season' button. The reason for this is that OOTP only keeps a small subset of stats after you proceed to the next season. If you look at a player in OOTP, you'll see quite alot of stats for the current season. But, in the career section, there are only a few stats. All the stats you don't see in the career section are gone from the data files when the season rolls over. Without the missing stats, many of the pages cannot be created.
If you use the career exporter, the stats from the previous season will be imported and displayed on the player pages. But there still won't be team/league pages for those years.
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