Regarding Boston--they will face a lot of questions this offseason, prospects or no prospects. They face losing their CF(Ellsbury), 1B(Napoli), C(Salty), Stephen Drew, and still need a closer, as Bailey may/may not be tendered a contract. The 2014 offseason is even messier--Pedroia's on an option year, Lester's a free agent, as are Dempster, David Ortiz among others.
It is unlikely Ellsbury resigns--as a Boras client, he will likely demand more than Boston's willing to pay--especially with Jackie Bradley Jr. on the way--Ellsbury will likely demand Carl Crawford money(about $15-20M). And Napoli hasn't been that great--his K's are way up and his OPS is down, and due to the lack of depth in free agency, will get significantly overpaid. Jarrod Saltalamacchia is looking at a huge raise because of his bat--he lacks behind the plane, as he is as bad or worse than JP Arencibia defensively.
The closer issue is a big problem--Koji Uehara won't last as a closer(injury history), and many of the free agent options this winter are lacking