The roads should not be that much of a problem, the storm is not supposed to be dropping snow at a blizzard rate (most areas are four to eight inches over 13 hours). That and the crews have not been out for storm after storm, so they are dying for some overtime (and in this area to stop having to pick up fallen trees according to one interview).
Go to google and map out the route in the morning and check the traffic and base your departure on that. If it's all yellow and red better get going, if not you can take your time.
Of course, it only takes one moron in an SUV who thinks they can still drive 85 mph so spin around a few times and cause issues, you can't really plan for that.
At 5 am there's only a 20% chance of snow, so you will probably be at the airport before anything really starts falling.
Assuming the airline flies the plane into Boston, you probably won't have any problems.