It seems like it should be relatively straight forward. but you might have to ask them (the town) what you need to confirm. Some towns are pickier than others for sure. We needed a curb cut permit (there were specifics on like how big the culvert had to be and how wide the driveway had to be at the street), and a permit for the house. I think that was it. The WW permit you already have. The well is already there. Is the barn worth saving? When I think VT barn... I think pretty basic, maybe not great foundation, etc.