SF - in the NL, teams use 5 and sometimes 6 OFs on a 25 man if one is a swing guy like Harris, Casto, or Orr. I'm with you on Bernardina for that role, though. I see the 4th slot as likely to be Harris (or Winn, if DPM is right). That player will get 400 ABs (+/- 50), while the 5th spot is a guy who gives you a few particular skills your roster does not have in abundance, like speed and defense. That last slot might be a scramble between Bernardina, Owens, and perhaps JMax, who would give you some PH pop. I'm still dumb enough to hope JMax can figure things out in AAA and become a Mike Cameron type (high K, great defense, good pop, OK OBP).
If Winn is brought in, then I think it shows they are more worried about Dukes keeping his job than they are concerned about a defensive complement to Willingham. I agree with DPM that this would make Harris a good trade chip. I don't see a need for both, though.
SF- as an aside, do you do most of your posts by hand held device (text or crackberry)? I've always guessed that some of your shorter and more caustic remarks are due to not being able to type out much to explain your view. That's why I don't get to hyper about the tone and don't snipe back.