I was pretty happy with my winter riding. We had about 2 weeks in which the roads were not clear, so i didn't ride then...otherwise about twice a week.
Basically I would look at the forecast and decide if it was too cold to ride. If it was anywhere in the upper 20's in the morning, I rode...the lowest I rode in was 25, with a face mask.
Often it would be about freezing or high 20's in the morning, then upper 30's or low 40's in the afternoon. I can handle that. What I can't handle is temperatures in the teens or single digits, or snow & ice covered roads, since I don't do any tire or bike switching. I own one bike, with 28mm tires...and ride it all year round.