Not too much of the electrical lingo.
The carrier -> the meter -> the main box -> various rooms of the house.
carrier -> the meter -> separate boxes -> various rooms of house.
My understanding is that you want as much power you could get to your workshop without over-loading the panel and or distribution system.
I would have a different wire going to two separate boxes. This way if the power goes out in the house or workshop it would not affect the other.
However I would also consider feeding back to the line itself and how that scenario would also go