Your biggest acquisition is Hardy, who had a terrible year and was demoted to the minors from a team not in the class of the Sox. Why do anything about SS at this point? The Sox can pick up Gonzalez's option and have a first class defender at SS who also hits some, enough if other needs on the team are addressed. There also is Lowrie, who will be the regular SS if he recovers and he could be a very solid hitter, certainly better than Hardy. And Iglesias will be coming up in a year or two. There is no reason to waste any resources addressing the SS position.
Assuming Wake comes back he is going to be a starter. At this point in his career I think there is a near zero chance he would be put in the bullpen. The odds, based on recent history, are that he will not be a regular starter for the entire season. Based on recent history the odds also are that one of the other pitchers, at least, will have a problem. The Sox do need to add another SP, but someone who will eat innings and keep the team in the game, not another 5 inning starter, or someone fragile. Based on his comments and the general inclination of Epstein I think he will make every effort to land a top-flight starter. Right now I think that is more likely than the Sox getting an impact bat, assuming Bay re-signs. If Bay does not re-sign then the focus will be on getting his replacement.
To remain competitive in the increasingly tougher AL East the Sox must get better. That means adding real talent, not the mediocrities who you proposed to add.

