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Just a few notes on testing this if you want to investigate whether you can make it work satisfactorily...
You could set up a practice/dummy league, like it seems you have, and run it through some test seasons. You could import any 30-team schedule (there are options in the historical & fictional schedule threads atop this forum), and it will work for any 30-team configuration even though the games will not be broken down by opponent the way you want them in the end. Assuming you have playoffs turned off, you would have to do something to make sure the game did not shut down the season and pop up the "Proceed to next season" button after the regular season in the imported schedule ends. What I think would cover that is manually adding an(other) All-Star Game about a month after the regular season ends, something like around the end of October. I think that will keep the season open, allowing you to manually add the games that would compose your playoffs one round at a time, then after you lay out the final series you can delete that ASG so that the season ends after that last series.
Once more that would be making the postseason technically regular season games within OOTP. Supposing you had 4 teams in your playoffs in that case, a semi-final round and final round. You could lay out the two 7-game semi-final series, and supposing they both ended in 5 or 6 games, delete the remaining games in those series and add the layout for the final series. One thing of which I am unsure is when the "Proceed to next season" button would pop up. Suppose the final series ended in 5 games, then you deleted the remaining games in that series from the schedule (plus that still out there ASG if you had not done that before beginning that final series). I think that after simulating a day in the game with no more games scheduled the rest of the year that the "Proceed" button will then show up, but I am not completely sure of that.
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