The best times to ski are after a Nor'Easter. Or there has been prolonged cold weather (2 weeks) with maybe Clippes. A great winter is 3-4 weeks without a significant rain event. Also, the first-time trails open for the season is great since no ice is present.
Finally, Spring is optimal when everything softens (sunny and 40 degrees+).
Even skiing under snow guns while areas resurface terrain is fun - especially where they can blow snow on multiple trails (Killington, Sunday River, Okemo, Mt Snow, Hunter, Wachusett, etc).
Flatter areas can ski OK during icy times due to grooming since the snow will hold up better than areas with steeper terrain (Bretton Woods, Okemo, Stratton, Butternut, Mt Sunapee, etc)
But there is A LOT of misery in between. You have to be so selective about your days. I avoided any days with high-pressure winds and cold temps. Freeze your ass off, and the snow can blow away.