Bingo, Seano. this is the big question.
The Sox F.O. has stated publicly that you can't contend every year and retain some sense of overall organizational strength, fiscal responsibility and a positive future. I believe it was Theo who said its 6-7 yrs out of every 10 that they felt the Sox could go for it, and that periodic rebuilding was essential to meeting the long-term organizational goals.
Yankees tend to operate under a different philosophy or so it appears...what they do this year will be very interesting.
Personally if they're going to rape their farm system I hope they do it going after more offense, like Carlos Lee...cuz if they were able to grab some established pitching (i.e. SMOLTZ) I'd be more concerned.