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Not saying skill isn't involved
I do think over the course of the season, things even out and the best teams reach the playoffs. As much as some of the games quirks annoy me and I think the variability is too great, in the end in usually works out. And there is skill in both maximizing your roster and maximizing your match-ups and usage.
But come playoff time, the small number of games means one abberant performance matters a great deal - and in any SIM, its random when they come (as compared to real life, where a real manager and real player makes real decisions that could lead to abnormal performances). That's where I think luck comes into play - if Randy Johnson gets shelled, its bad luck, as it equally if not more likely he'd be dominating. So I think weighting the playoffs too highly in a best team measure is questionable. I know its more exciting and memorable to win it all, but winning a bunch of games is fun as well.
I speak from experience here - my longest winning streak ever in PB came in the playoffs - after losing game 1 of series 1, I won 12 in a row. If we were to replay those playoffs over and over, I doubt I'd even make the WS half the time. It was a great, solid team, but gotta be honest that it was beatable and things went my way.
Fred C