I agree with MossRoad that you should consider a farm panel. You don't tell us the eventual extent of your plans, but if you are thinking you will build a house at some point, you could set a meter and panel on a treated wood pedestal, I like to use two 4X4's set in the ground with 2X8 or more boards nailed or screwed to them to create a surface to mount the equipment. I don't like plywood so much because it eventually delaminates. A good choice for the panel would be one designed to serve a mobile home, which has a 200 amp main breaker which feeds lugs at the bottom of the panel for service to the house , but also has 8 additional breaker spaces to feed outbuildings or whatever. So, if your house will have average electrical needs and your barn and say shop aren't too energy hungry, that might be all you need. If your plans are more elaborate with a large barn and shop, just do two panels for a 400 amp service. For the barn, you can just use two of the breakers spaces to mount a 100 amp breaker to serve the barn. The lugs at the bottom of the panel wouldn't be used until you build the house. You don't say whether the nearby transformer is on a pole or is pad mounted, but Dominion in Virginia typically will run the service for a residence underground for free, whether it's from the pole, or from the pad. You could also just have a overhead service drop to a pole, but it would be a private pole, you'd have to set it.
I'm not sure what Domnion would do with a barn coming first, but it's worth asking. You will need a permit for the service, and the panel in the barn if you set up a farm panel as suggested, but the wiring in the barn won't need inspections, at least that's the way it works in Albemarle County. As far as talking to your local inspections department goes, one good rule is to not tell them anything they don't ask for, that'll avoid a fair amount of trouble. The other rule is to avoid arguments, they get to interpret the code and they can screw you up if you get on the wrong side of them. I've generally found inspection departments to be willing to help you if you ask questions and don't try to put something over on them. Usually, non commercial site plans don't have to be fancy, you should be able to stake out what you want to do, measure to the property lines reasonably accurately, and draw something up. You can ask them for some guidance on what they want. Good luck with the project!