I'm guessing that we're looking at the original Service to the building and that you're standing on the roof of a later addition?
If so, I agree that there should be something in the Code to address stuff that is done in the reverse of the normal sequence of construction that people think of.
I've know of folks who wanted a garage when they had the house built, but changing the route of the overhead drop drove the cost up; so they bought the house without the garage and added it the next year. Almost no clearance for the wires, but no way to force them to fix it either.
Just how many different voltage systems are coming up here?? Typically (at least over here) the POCO will bring one drop and tap off of it to feed multiple meters. There's also a couple service entrances that are quite oversized for the size of the feeders coming out of them. Seeing the prehistoric weatherheads and such I'm guessing this install to be from between 1900 & 1920's.