I'm well aware of how baseball works in terms of short series and small sample sizes, and believe that trying to predict individual performance in the playoffs is an exercise in futility. To say that Sabathia will be outpitched by Verlander or vice-versa is just a guess, since any player can have a good/bad game on any given day.
I prefer to look at the strengths and weaknesses of each team and go from there. I'll start with sox/yanks because I can post stuff with them without looking up anything.
Yankees - good starting pitching, incredible lineup, great 8th and 9th bullpen guys, and the best team at playing the same level at home and on the road. Weakness - inconsistency throughout the year from Burnett/Chamberlain, Damon's defense in LF, Swisher's occasional head scratching plays in RF.
Sox - good starting pitching (great #1, #2), good lineup, good bullpen, great closer. Weakness - different team away from Fenway (.856 home OPS vs. .753 on the road), lineup can be streaky, potential recent health concerns with Beckett and Lester, inconsistency from #3 and #4 starters.