I think if you're the Red Sox, you gotta sign Schilling on his terms, 1 year at $13 mil. Provided they re-sign Lowell, this team has a serious shot at winning again next year (unlike in 2005) but without Schilling, I don't think the Sox have enough depth in the rotation to be a serious contender. I also don't think they'd be able to replace Schilling through free agency, not with the lack of depth hitting the market.
So with Schilling, you're looking at a rotation of Beckett, Dice-K, Schilling, Lester, Buchholz/Wakefield which is a very good rotation. Without Schilling, you have too many question marks to consider the rotation a real stength
Then for 2009, you'd think Lester, Dice-K and Buchholz will be progressed in their development enough to be considered locks for the rotation so then it would be the perfect time for Schilling and probably Wakefield to leave Boston