Like many things in life, I imagine a lot of what we prefer is related to what we grew up with and what we are used to. I spent a winter living in the Denver area and a year in France, both places admittedly have relatively wild weather, but still harsher than what I grew up with. As a kid I would read about snow and thought it sounded so fun and romantic. I completely agree that heat sucks because you can only take off so many clothes and if you are still hot, all you can do is suffer. If you have the right clothes, cold can be okay, as long as you don't have to shovel or scrape or drive.
I travel regularly though not frequent for work across the US. I have only ever been on one trip where I wasn't immensely grateful to be back home again after, and that was this lovely boondoggle trip to the San Juan islands. :) I certainly hear people appreciate four seasons and more power to you. It is way more important to me to never have to think about what measures I have to take to mentally and physically steel myself to fight the uncomfortable elements. The older I get the greater a source of joy that is for me. Again, to each their own.