Hi Kevin and welcome!
I live in Austin, TX, and have the good fortune to be able to ride year round. It does get quite cold here sometimes and clothing is the key.
I find that as long as my feet, head, and hands are warm I'm okay. I also hate wind but you know all about that living in Chicago.
I did a ride last April where the temp. was around 40 and the wind was so bad that many people were out of their saddles on a steep decline!
I'd love to visit your shop the next time I'm up there. It looks great.
I bet one legend that keeps recurring throughout history, in every culture, is the story of Popeye.