...and then hope for a couple of breaks to get them a 50/50 shot at playing in the Division Series?
The goal here has to be 95-win talent that makes the WC a disappointment, not a patchwork team/lottery ticket. Holland probably can't be a rotation-topper on a 95-win team, but we know can be an innings-eater on a 98-win Pythag team. Ellsbury will never be on another 95-win team in Boston, because he'll be somewhere else in 2014.
Actually, the goal is to win the World Series. That's certainly a lot more likely when you have a 95 win team than say an 89 win team but it's not entirely clear that it's worth giving up a chance at an 89 win team for a slightly larger but not precisely measurable chance at having a 95 win team.
This is why trading for Andrus makes minimal sense. Sure, you get a good shortstop and we could use one, but then we end up going into the next off season talking about trading Andrus.
I think the way to maximize the likelihood of winning the World Series over the next 3-5 years is to re-sign Ortiz, bring in competent but not spectacular players at first, left, and right, keep Ellsbury and see what happens with 2013 and aggressively mix in Bogaerts, Brentz, Bradley, Barnes, de la Rosa, Lavarnway, Webster, and whoever else I am missing.
Hell, depending on how Buchholz, Doubront, Lackey, de la Rosa, and Webster are doing, the Sox could conceivably be in a position to offer Lester and Ellsbury as a package at the 2013 deadline and have it be a very attractive package.