I go 3-4x per season. I only go for a seasonal warmup. Big Acorn is my favorite hill. I've not been too impressed with Highlands the past few years, especially the mogul section. The snow quality never has been great, either too wet or iced over. But give me a shout if you want to meet one day, week days are best for me.
I don't like Wintergreen's season pass. Its only good from 12:30 to close on Sunday, whereas Massanutten's is good all day Sunday, and Saturday for the night session. I can drive up Saturday, ride that night, sleep/drink and then ride all day Sunday.
That'd be better if I didn't work Mon-Fri. I'd probably still end up with the Massanutten pass though as I've got a friend I can stay with there, and free room for the night is worth the 45 minute longer drive.