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Humans are smarter than the AI - even when talking about your average gamer vs Markus' AI. So the more things you handle yourself, the "easier" it will be. Of course, it also comes down to effort: if you play out every game, and win a championship after 3 seasons, you might play that game for a full year. Someone who skips over chunks of the year may only win after year 5, but can get 10 seasons in for your 3.
So I wouldn't treat it as "playing out games makes it easier to win, so I don't want to do that". I mean, you can play out every game, but if you never care about trading for players, then you might not win. Conversely, letting the AI sim all your games is harder, but if you spend 3 hours scouring through everyone's farm for guys who they don't want, and meddle for every last ounce of every trade you do, you'll likely easily build a champion from that.
So after this rambling, I would say play it however you want to play. Personally I get more fun over the course of a season being GM, but I do like playing out some games, so I more closely manage in the playoffs. I could very well change to playing out every game individually, but I think I would find it frustrating that I don't progress along very far. Even if it just takes 5 minutes per game, playing out a full season is still 13 hours of game-time, which added to time it takes to trade, sign players, draft, eat... takes up too much of my time.
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