I don’t understand how this happens with commercial vehicles you would think their routes are planned out to properly account for their size.

By the looks of it, it wasn't that it was over height, it's that they were driving around with the lift to the bed raised and that's what was over the limit.

Truck drivers are usually given an address. Bus/motorcoach operators (not public transit) might receive "lefts and rights" to a location.

I have a feeling that when they "Storrow", they are using GPS for 4 wheelers. Commercial GPS units have information that commercial drivers need, such as forbidden roads.

I had to get a bus to Kenmore legally, without GPS. I would have jumped on Storrow in a car. You have to run through streets in your brain & it is really easy to get caught up on Storrow especially around Charles St.

It'd be a neat feature to have some kind of failsafe to prevent a driver from doing that. I can barely go 5 ft before my car starts an annoying beep if myself or any passenger hasn't buckled their seatbelt.

wasn't there a thing where UPS planned all their routes to minimize/avoid left hand turns before they realized the net impact on fuel was worse?

Yes they tried that and every CDL holder in the US collectively guffawed.