With the flexibility the Sox have on the starting pitching staff (5 good starters, and a few promising arms in the minors) and a young capable bullpen, I'd really like to see Hahn be proactive this year in trades and a few relatively inexpensive free agents.
Regardless of the success we had this year, the core of the team is getting older and some of them are flawed hitters. I wouldn't be averse to deal one or two and bring in some quality young talent at positions of need.
IMO, the worst path the Sox can follow is bring back the primarily same team as last year and plug Flowers in at C and Morel in at 3B, which only further weakens our poor situational/pressure hitting offense.
Another big issue is getting a capable bench. It would be nice to have guys that Robin can put in a day or two each week and not have our main players wear down in September.