Getting power to the new shop

The power coming to my house is fed overhead from a line that travels about 200 ft to the transformer. So if I'm understanding it correctly it does come from the transformer directly. Yes, I meant a down guy going to the customer owned pole. I think I need to definitely ask the question about bringing in a larger 300 amp service to my house and then subpanel to my shop. Initially my buddy said it would be quite high in price, but the way it is sounding it may actually be a better cheaper alternative.