The sox are going to have an interesting dilemma come this offseason. They will have holes in spots that have solid prospects lined up to take over. But if you are going to go for the gusto, having 3 spots manned by a rookie typically spells doom for your playoff chances in year 1.
FA's after 2013 include (and I think Lester's option is picked up)
1B- Mike Napoli (2.2 WAR)
CF- Jacoby Ellsbury (5.1WAR)
C- Jarrod Saltalamacchia (2.6 WAR)
SS- Stephen Drew (2.3 WAR)
CL- Joel Hanrahan
LHP- Matt Thornton ($6 mil option for 2014)
For the position players, that is 12.2 WAR that needs to be replaced. And the likelihood is, all of the above players hit the market and find lucrative deals elsewhere.
So let's say they go the young route. Cecchini is playing well in AA, he could move up to the bigs at 3b. That would move Middlebrooks over to 1b and Bogaerts would take over at SS. You have JBJ taking over in CF and you'd have to scour the market for a C, or decide it is Lavarnway's time. While that decision likely would lead to further long term success, it would not yield a playoff caliber roster come 2014.