I don't buy this "take prospects with bloated contracts" idea. Is there any case in recent history where someone did this? MLB is a copycat league, and this strategy has not shown to be successful. Plus I don't see Hahn taking bad contracts now that he's finally clearing payroll, even if we get a few "B" prospects in the deal(s).
IMO, the Sox are going to have to spend on hitters this offseason, as we have a very weak team without them, and none of our impact prospects are close to ready other than Garcia.
We should try to move Rios before Sept 1st regardless of the return. We should still be able to get something decent for him.
I see a opening day lineup of:
2B : Beckham
DH: Dunn (nobody is taking his contract until next deadline)
1B: <free agent>
LF: <free agent> or Viciedo
3B: <free agent> or Keppinger
And I'm not talking about the top free agents either, though Granderson and Morneau at below-market deals due to injury risk would be tasty. The Sox could add some good bats for at market prices in January after the big names have signed.