It's an amazing drive. I've done it several times and it gets better each time. Just check the CDOT road conditions website before you go for signs of bad conditions, and any mention of icy conditions or snow and waive off. I will say that the road up to Independence Pass (both sides) is really skinny in places without guardrails (with big drops if you go off). In fact on the way down into Aspen it effectively narrows to one lane in places. They take this into consideration when they open the road so I wouldn't worry too much.