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I like your idea but I think trading would suffer from that many sims per week. If you did 3 sims a week with a month per sim there would still be room for some trade talk and time for those transactions to take place.
I also think you'd benefit from setting the draft pool to appear as early as possible and then using Getch's util to run the draft right away. Import what you finish by the draft and then use the in-game lists to finish the draft.
I also wouldn't fill the minors with fictional players if you are doing historical. Just do simple 3 level minors to start with until all teams could field full rosters there. Then add a short-season league.
I don't like the pick lottery.
If you end up doing something like this shoot me a PM.
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