As you probably know I train in a cemetery. I have found this location to be the best for me to deal with winter for a number of reasons.
1. It is only 100 yards from my house.
2. It is cleared as well or better than the roads and certainly much better than sidewalks.
3. Running the 1/3 mile loop repeatedly, if there are any icey patches they can be anticipated.
4. Running the small loops means that you don't face the wind for any extended time, thus evening out the wind chill
5. As the temperature goes down I just put on extra layers, generally just cotton, not a particular fan of tech materials.
6. Going out the door is no big deal if it is cold or snowing. I don't like going out into heavy rain although if it starts during the run that's sort of OK. A coating of freezing rain makes running impossible. This seems to happen less than once a year though.
7. To a minor extent I time my runs to avoid a particularly bad weather event.