I find the challenge of choosing the right gear for conditions to be satisfying. I don't mind riding in the winter as long as it's above, say, 30 degrees and sunny and the roads are clear. That happens more often than you might think up here in central NYS. Be aware (you'll find out soon enough) that the colder it is, the shorter your ride is going to be. And, you're going to get cold no matter how well you plan and equip yourself. That's just part of the experience.

That said, I enjoy riding in the winter. I appreciate being "hardened off" come spring so that I can run around in shirt sleeves while everyone else is wearing jackets and sweaters.