You'd be surprised at how random the traffic patterns are in Boston. Sometimes you just get dealt with an absolutely terrible hand (I don't commute, this is just my experience on occasional drives during the work week with random congestion). 11pm is no problem, but 2pm could vary.

This is what I would call an expert commute-- the kind of thing that is much easier to navigate when you have a year under your belt to contextualize it. At the very least, you should come out here and drive it once at noon to test your tolerance-- how tolerable really depends on the person.