Definitely go on a clear day. We went up day of first snow in Sept 2013 when it cleared up in the late afternoon. Because it was 10F and 30 mph winds outside, we were unable to frolic in the snow as you see many other in pictures. There is still plenty to see and do and you can still get outside on the observation deck.
Your Half Fare card helps much with the price. Still spendy, but how often are you going to be here? Takes 50 minutes up and 40 minutes down. Two 5 minute stops on the way up to look out the observation windows. You go from 7000' to 11,500' pretty quickly so take care if you don't take altitude well.
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