What do I do about winter? Laugh, and go for a swim. Okay, sorry, Floridian attitude there. Seriously, though, this part of Florida does get cold, with hard freezes and even occasional risks of very slight dustings of snow.
Sleeping bag gets added to BOB, thin long underwear goes into emergency clothing/uniforms bag, and spare fleece jacket stays in car. That's about it for me.
The real danger here is that nobody respects or knows how to drive on icy roads. I once stopped at at least a half dozen wrecks on the way to work one winter morning, including one with serious injuries.