You live in Chicago so you know how to deal with cold weather and such! Your winter conditions are probably not that much different than being on a summit here in Colorado…below 0 degs F, wind, and such. It sounds like you’re mainly interested in radio and battery related stuff in cold conditions. You posted that you’re only climbing about 30 minutes from the trailhead so you don’t need to deal with all the extra gear that is required for the backcountry. I assume you already know how to deal with car related stuff in cold conditions.
So, I think the main thing to deal with is extra batteries for your cell phone and rig. Keeping them warm is a good idea. I carry my phone and batteries close to my chest in the winter. You should also have some protection from the wind…ie Bothy bag, tarp, etc…and hopefully you can find an operating position out of the wind. Having a thermos full of warm tea/coffee is also nice to have. I also bring some thinner gloves for operating the radio and paddle. Hands will suffer from the cold first but you already know that!
Of course, if you venture further into the backcountry and climb harder mountains, you’ll need more equipment as others have posted.