Fantastic in the snowy season.  Getting to Windy Gap usually requires spikes or crampons and axe, but it's well worth the effort.  There's also year-round running water at Little Jimmy Springs.  Right by PCT.  And also close to another Gem.  South Mt. Hawkins, but that one is unorganized, you'll have to search for a place for your bivy to lay if you set up there.

I've been to Jimmy multiple times in dirt, snow, and even a little rain.  It's not overly windy, because it's protected by a bunch of trees.  The peaks and saddles around it can get a little windy.