He will attempt to re-sign Ross, but Ross had a career year, his best since 2009 when he hit 24 HRs and hit .270. So, he will want at least 4/30M and I would be surprised if the Sox offer more than 2/12M. My guess is he goes elsewhere.
Papi would be my guess to land first, and they will offer him 2/27M. whether he takes it or not is another story.
Ellsbury is on the block, he will be traded and the Sox will attempt to sign the FA Bourn to play CF unless the Braves make him a qualifying offer. But again the Sox are usually short on time, and Bourn will looking for at least 5 years. If they offer 5/40M, it could be enough.
1B. This is an issue. LaRoche is an FA but the Nats will likely exercise to 10M mutual option. The Sox best bet is to reacquire Youkilis to play 1B.
A hole remains in RF (and really has for a number of years). I would like to see the Sox try to work a deal Quentin. He's got 3 years left on his 4/37.M, and is a steal at that price. Would likely take a couple of top prospects to get him though.
Catcher is something the Sox need to look real hard at. I used to be real high on Lavarnway but after watching him late this year, he did not impress me much. It was a mistake to let Shoppach go, and Salty is just not a solid catcher. Napoli would be my first choice then Martin or Laird (although NY will likely want to retain Martin's services). Trade Salty, obtain a veteran catcher and groom Lavarnway.
As far as the pitching goes, I think Lackey will rebound. I'm just not so sure about Buchholz and Lester. There are some intriguing FAs out there and I think we need to get at least two of the best ones available.
That's my take.