Losing our 2 best, and really only significant RH'd bats in JT and Duvall, does make adding a RH'd bat to CF or RF make sense. We could even bring Duvall back to play mostly RF and be insurance against a Rafaela struggle in CF. I can see Dugo being traded.
What Dugo brings back in trade is not going to be ground-shaking, unless part of a larger package. If somehow we can get a solid SP'er for Dugo and some prospects not named Mayer, Anthony or Teel, I think we have to pull the trigger. One problem is a team wanting Dugo's 1 year deal is probably not looking to add prospects while giving up a solid SP'er. Maybe 3 teams would be needed:
Dugo to team A
Prospects from team A and from the Sox to team B
Team B sends a solid SP'er to the Sox
I'm not talking an ace, here, unless top prospect(s) are involved.