Is David Ortiz coming back? That could be cleared up by Wednesday, if the slugger accepts Boston's offer of arbitration. If Ortiz declines, the Red Sox might then increase their efforts to re-sign him to a multiyear deal.
There is also a decision to be made at closer. Will the Red Sox sign a veteran off the market or promote Daniel Bard to that position?
If Bard doesn't close, there's a chance he will be moved to the rotation. As Cherington said recently, Bard is at the point in his career where he's ready to accept more responsibility.
Right field is another position of uncertainty at this hour. Ryan Kalish and Josh Reddick, two young left-handed hitters, could be part of the solution.
But Cherington wants a right-handed bat, and Michael Cuddyer is a name that's come up a lot.
"We're continuing to work on building pitching depth," Cherington said. "We've done a lot of work with respect to talking to free agents and teams and getting a feel for the landscape of the market this winter. There will be additions to the pitching staff. As I've said, we'd like to add a right-handed complement -- someone to balance out the lineup a little bit. We'll continue to work on those things."
After last year's blockbuster moves -- the trade for Adrian Gonzalez and the signing of Carl Crawford -- the Red Sox might be in line to have a more subtle winter this time around.
Then again, you never know.
"We're not going to rule out any avenue, whether it's free agency or anything," said Red Sox president/CEO Larry Lucchino. "I said once before, we're going to explore it with healthy skepticism, but we're going to explore every possibility: trades, free agents, international signings, everything. Ben has got all those things going on these days."
Check redsox.com for frequent updates throughout the Meetings. Cherington will hold daily briefings with the Boston press. Valentine will have a briefing with the media on Wednesday.
Feel free to use the comments platform to express what you think the Red Sox should work on during the Winter Meetings.
Ian Browne is a reporter for MLB.com. Read his blog, Brownie Points, and follow him on Twitter @IanMBrowne. This story was not subject to the approval of Major League Baseball or its clubs.