It's a question many of us this side of the pond dwell upon, too, at this time of year. Don't know if you've ever been to the UK but we can have four seasons in a day - twice - if there's a heavy system blowing across from the west. Northerly and easterly air-flows tend to be more predictable - i.e. get your thermals on 'cos it's gonna be cold and probably snowy!
Apart from a few specific expeditions to places I've needed to / wanted to visit, it's easy to become a 'fair-weather' photographer. However, this year I've set myself a project to shoot a calendar of the area in which I live (East Anglia - which is a term for Cambridgeshire, Norfolk, Suffolk and Essex).
By definition, it needs to be outdoors, as a shopping mall looks mostly the same any time of year - except, perhaps, Christmas. It's also a generally very flat area, so lots of big skies and cloud formations.
My biggest 'pet hate' is rain. Not because I don't like getting wet but because I don't like my kit getting wet. So, I'll be examining some waterproofing systems and buying some extra bags of silica gel to store with the camera after it's been allowed to dry for a couple of days in a warm room.
Thanks for this thread, it's sort of galvanised my resolve to get out and amongst it - come what may, weather-wise.