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I started with OOTP11 after it had been released for a while. I had played other baseball sims, so I just jumped in and created a historical league. I used the manual along the way, and read the forum on a daily basis to keep up with the latest comments from users. I searched the forum and/or Googled a question whenever I wanted to do something that wasn't clear to me. I asked a couple of questions here and got very straight-forward and helpful answers.
Given your past experience, I am sure that you will pick it up in no time. My advice is to start with a league that you won't mind dumping after a few weeks and save your best idea for the second attempt.
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