The last time I drove in Boston...
I would've settled for a decent set of street signs. On several major highways, the signs showed what road you're on but not the names of the cross streets. I was driving south on an interstate and a major fork was approaching. It would've been helpful if they'd actually identified the roads so I didn't have to guess which one to take.
That was in 1992, so maybe things are better today. Just in case, I don't plan on ever driving in Boston again. You might mention experiences like mine to your tourism officials. The Boston driving experience is bad for repeat visits.