The majority of CDL holders get around fine, but since Boston's a big educational center, you get all the out-of-towners moving in for the school year, and those with their rent-a-trucks make life miserable for everybody, failing to plan out the route.
I heard one story about a daughter of a computer biz giant doing just that.
Do those sat navigation companies take into account clearance restrictions when giving you directions? (snow and repaving excluded, of course)
I'll say, no, they don't.
One of the mapping services has a disclaimer, advising you to check actual road conditions and routes.