Yeah there are plenty of holes in it. You just named one, its pretty streaky with the left/right handed batters. Another one is Jacoby might be blocked from stealing a base too often.
Maybe this would work better:
1. Drew
2. Youkilis
3. Pedroia
4. Ortiz
5. Bay
6. Varitek
7. Lowell
8. Lowrie
9. Ellsbury
First off, the left/right hand inbalance is reduced. Got two on-base machines at the top of the lineup, and Pedroia would serve very well as a third hitter behind them. He'd rack up the RBI's, though Drew and Youk's lack of speed might hinder that somewhat, not to mention having Ortiz (hopefully healthy and effective) batting right behind him. Ellsbury at the bottom of the lineup, if he gets on base he can be pushed into scoring position by either Drew or Youk getting on, which they do very well. Varitek at 6 might be a bit of a stretch, I admit.