I think the Coco Crisp trade is unlikely and it would be costly in terms of prospects. If the Sox have to give up any blue-chippers, i.e., Lester, to get Crisp, it would have been better to keep Damon. IMO Crisp does not have that high of a ceiling. He'll be lucky to be as good as Damon.
I'm also not sold on Reed. I have heard that he is very strong defensively. His stick has been nothing to brag about and speed (base-stealing) is not part of his game. With Roberts, he has defensive skills. His offense is no worse than Reed's and he is a weapon on the bases. I'd prefer to get Roberts for a year or two until the kids on the farm are ready. That being said, SD has to drop the demand to take Williams. That would make no sense.