I don't know how you outside guys do it. into the 40's and I'm not enjoying it, although I have no outside setup or heaters or anything.
I prefer to be outside smoking, on the golf course ! But I just can't sit out by myself in cold weather and have a cigar and enjoy it.
Luckily, I have a very understanding wife and was able to convert my office / man cave into a smoking room.
As long as I'm contained to one room and don't stink up the house it's all good. And it allows me to smoke daily...

So I guess I'm not very dedicated when it comes to the cold, but I was dedicated enough to solve that problem !