I think it is the beauty of iOOTP (and other text-sim games as well) that you can find your own style of play. I, for example, play out a few games to start the season (get a feel for my team), then change to simulating and later in the season, when it comes down to the last games and I'm in the Playoff Race, I switch back to playing out my games. The Playoffs are the same, nothing more exciting then a Game 7 going in Extra Innings.
I read another nice way to play today on our board: someone is so addicted to play iOOTP (at work) that he allows himself just one game, basically following the real MLB season on his device. For me it is easy: my job is to play iOOTP.