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I look at OOTP as more of a grand strategy title where I can amass a centuries worth of statistics and history rather than an operational day to day sim.
I play out about four games a year, sim the rest. I try to sim a season every few days. I check monthly at the players stats and make roster changes. Biggest enjoyment is juggling the roster with financials, weighing whether to lock up that veteran to a long contract, and seeing the farm system progress.
June draft is the highlight of my season, playoffs are just something to get through so I can get to the meat of the game which is keeping which veterans, cutting which under-performing minor leaguers, proposing long term contract extensions, and signing which blue chip free agents.
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