The drive from c. spgs isn't too bad if you take 24 to 9 to Breckenridge. Only problem is you end up at Breckenridge.
I lived in the Springs for a few years and always enjoyed the drive through southpark to Breck, sure beats the hell out of I-70. From my perspective, consider yourself lucky.
I'd second the recomendation of lessons and plenty of time at small resorts. Monarch would be a good bet if driving from the springs.
Right on Andy, boots are the key, regardless of how you slide down the mountain.
So far as winter clothing, so long as the temp is below 30 I wear: Expedition weight Gore-Tex shell, fleece jacket, polypro long underwear on top and lightweight fleece pants under a pair of rugged snow pants. So long as there's lots of zippers for cooling off, you'll be toasty down to 0 with that getup.
Hope you take to it like a duck to water!