Skill level, I would say intermediate to advanced. We usually have a season pass at blue mountain. Some park but mostly downhill. I would like to try half pipe again, it's been about ten years. My husband loves glades runs. Also we're staying for a couple days so nightlife and resort are important too.
Highlands had a nice halfpipe last season, both highlands and mountain had nice kickers too if that's your thing.
Here is a map I made of the Michigan resorts
, you can see where they are and some general information about them.
I could be wrong but while Highlands is farther north, I think it's closer to off resort nightlife. Petoskey is within 15-20 minutes of the resort and I've enjoyed a good pub or two there.
Dave was right about Crystal having a nice resort feel and good restaurants despite the small size but I'm not sure about the off site offerings in/around Thompsonville.
If you're just sticking to the resort then I know Boyne Mountain has the rep of being a party atmosphere. I just don't know that first hand.
If it were me choosing, I'd go Highlands.