I live in Charlottesville. Wintergreen is pretty bad. The biggest jump they had this year was maybe a 20' table top, and the rails aren't great but they did buy a 10' rainbow box and a c-box this year. The park is maybe 200 yards long and on weekends is so packed with people that it isn't worth skiing. Otherwise, the rest of the mountain is incredibly easy. The Highlands, the "experts only" area is about as difficult as say a blue out west. Except it is usually really icy so that makes it a little more interesting. The lift lines on weekends are absurd. A normal wait at the Dobie lift is like 20-30 minutes and it only takes 30 seconds to ski from top to bottem. The Big Acorn lift is usually a 15 or so minute wait but those slopes only take a minute to get down. The highlands lift is nice though, you usually only have to wait five minutes.
If you go up on weekdays lift lines are nonexistant, but they dont shape any jumps during the week so the lips are torn up and the landings are really canoed out.
Every year on april 1st and 2nd, or there about, they make all of dobie into a terrain park which is pretty cool, but the jumps get torn up after a few hours.