I don't think that we have 'too many holes' to fill. Again, I think our team looks pretty good as is.
I am surprised that no one seems to be concerned with the potential health of our starting rotation. If our rotation is healthy, they should be one of the top rotations in baseball. If ERod does not bounce back from his surgery as quickly or as strongly as expected, and/or if Price has significant elbow issues again, then that paints a whole different light on our rotation. After this past season, I do not have a lot of confidence in Price making it through next season without spending a lot of time on the DL.
I would look for a #2/3 type pitcher on a relatively short contract (easier said than done, I know), and sign JD Martinez, and call it a day outside of tweaks to the pen and the bench. In both cases of the pitcher and JD, I would offer more money per year to get fewer years.
Honestly, if Dombrowski did nothing this offseason, I would expect the Sox to be back in the playoffs.