I have boarded the following local locations:
Massanutten, Wintergreen, Snow Shoe, Timberline, Canaan, White Tail, Ski Liberty, 7 springs.
If you enjoy riding park predominantly, then a season pass to Wintergreen would be the way to go. They have pretty decent size hits if the weather holds out, but the landings are straight ice lol. Also, the 'double black' they have at Wintergreen is a pretty fun run, and it more or less has it's only lift.
I cannot recommend Massanutten unless you're a beginner and it's the closest thing to you.
Of the above mentioned resorts, Timberline is my favorite, though I haven't seen all of Canaan (family trip with wives = not enough time on the hill). Timberline has great snow, and if you rip down their runs they can present a challenge even for the most seasoned boarder. Timberline reminds me the most of Rockies, albeit the runs are about 1/10th the length. This place has very little in things to do other than ski/board. They used to have really good beer on tap, but they stopped carrying it last year. I hope they bring it back (can never remember the name)
Snowshoe is definitely worth a trip if you haven't been there. Lots of runs, difficulty is an intermediate. It will take you all day to see that place, your legs will be tired. Their park is also nice, their hits have smooth landings, and it's pretty empty on the weekdays. I would not go on a Saturday or Sunday though, because there's at least one green trail that leads to every lift, so there's 8 million people in line for the lift, and that gets old really quickly.
I thought 7 Springs was nice, but we went too early in the season, so there wasn't much snow. I wouldn't mind going again if they had the best snow.
Whitetail has a pipe, and a couple parks. The main park usually has two really nice and big hits that are shaped really well. Just don't board all the way down, and there's a 2-person chair that services the park and the park only. If you want to throw down some park laps, this is the place to do it. The runs here are also very nice, and the lifts serve only 1 level of difficulty each (for the most part) which means if you're riding black, you're making plenty of laps.
Liberty is nice, but I prefer Whitetail better. Very similar though.
A trip out west is definitely a lot of fun. I have boarded Park City, and about half the resorts in Montana. You simply cannot imagine the difference between western resorts and local ones. Simply not the same sport.
There is not a single run at the local resorts I've mentioned that I wouldn't go down, and I'm usually the fastest person on the hill. Out west I generally stick to blues and greens and I'm generally the slowest guy on the hill. So, my advice to you: unless you can absolutely rip down the local stuff, then you're not going to get the most out of a Western trip.
Final Verdict: If you have your own gear and have already ridden 15+ days and are comfortable on blues and blacks, take just a few trips to WV if you haven't been there. You will enjoy it thoroughly. Squeeze in a road trip to Vermont if you can.
Once you go out west and you get a taste, that's all you're going to want to do, lol.
Anyway, hope this helps.
Absolutely helps! Yeah, that's the only crappy part is that we had season passes to Wintergreen last year and they ended up not even having all of their slopes open all season because it kept raining instead of snowing. I've been to 7 springs and vaguely remember having fun, and was definitely wanting to take a trip out to timberline since I've never been before. One of my friends had gone and said for the variety you get, it's really the best option. I agree with what you said about Massanutten though, we usually do their Monday night madness and are nearly bored with it after about the first 30 runs unless you have races or are playing a slope game or something. I was pondering on a trip up north since I have relatives that live in Jersey so I could explore places like Camelback but I've heard to wait in their lift lines, you might want to bring a lawn chair for how long they are. It seems like with the way the weather is currently going, I need to hurry up and make up my mind!! Can't wait to see the white stuff falling!