Not necessarily. For the season as a whole, you don't really care about individual contests -- you're just looking at beating the averages.
For a playoff, things are different... you're in a match-up against a single team that is better than the average team. I would argue that money and luck plays a much bigger role in the playoffs for a smaller team. If you're playing the Red Sox or Yankees, chances are that all of the key players qualify as "best talent", while your budget forced you to choose your investments more carefully or choose players with less-known ability.
>I would argue that money and luck plays a much bigger role in the playoffs for a smaller team
Luck plays a much bigger role for all teams in the playoffs. That's the nature of the small sample size. I'm not convinced that money plays a bigger role in the playoffs for a given team than in the regular season.
One valid consideration, in the context of the 2002 A's, could be that they built their success by adding wins on the margins. Put another way, the 2002 A's on average were one of the best teams in baseball, but the playoffs put greater emphasis on the "top" of the team, or the best players. That A's team was short on all-star talent, but made up for it by adding wins at the margins. But adding 2 wins by intelligently selecting a fifth starter doesn't matter in the playoffs, because said fifth starter will pitch out of the bullpen, if at all.
However, baseball is radically different than it was in 2002 and I don't think that still applies to the same extent. Almost every team is using the kind of player evaluation that Beane was using in 2002. There's still some fogey Joe Morgan types that just happen to be running baseball teams now, but they are by far in the minority. So now you have to be even smarter than Beane was at the time (see Friedman and the Rays) to be competitive on a budget. But the way Friedman et al. are doing it now isn't subject to the same implications as the way Beane did it when RBI was considered a good metric for talent evaluation.
For a playoff, things are different... you're in a match-up against a single team that is better than the average team. I would argue that money and luck plays a much bigger role in the playoffs for a smaller team. If you're playing the Red Sox or Yankees, chances are that all of the key players qualify as "best talent", while your budget forced you to choose your investments more carefully or choose players with less-known ability.