As far as the whole Holliday v Bay debate, I think that Holliday is the better player and will be the better fit, but I fear he's going to command a Teixeira-like contract and Boras will force the team that signs him to overpay for him.
I don't think either sign with their respective teams during the exclusive window, as both know the value of their contracts could be tied to the other.
I'd like to see the Sox add Holliday personally, but Bay might be the safer play because Boras can drag out negotiations to the bitter end, and if the Yankees or another team swoop in and drastically overpay for Holliday/Bay the Sox could be caught with their pants down, a la MT last season.
They need one to play LF next season. I don't like the idea of a Drew-Ellsbury-Reddick outfield come opening day.