You could probably do it especially if you get in tight with the Maggots at TGR. Learn the forum flavor well there before you post. You'll still get JONGed but you'll know how to respond to it. Get in tight there and you should find rides.
January is pretty cold in Winter Park. It can get down to -35 F (-37 C) at night. It's a little warmer at lower elevations and in other CO valleys. The wind can get pretty miserable sometimes on the tops of peaks.
I mainly work weekends at Winter Park so I'm not much help there. I don't generally drive through Boulder either. If you can make it to the Park and Ride Dinosaur Lots in Golden (they are on I-70) you'll find a ride. There are four lots but most people meetup in Wooley Mammouth lot. I think there is a bus that runs from Boulder to Golden. Check with the RTD website. http://www.rtd-denver.com/