Hi mtailnm,
It'll be mostly flat with a couple of hills. Granny gear isn't a strict necessity. I'll be riding through the city but taking bike paths where possible to reduce the number of stops. It does rain here and I will be biking through the rain. I probably won't winter commute through the snow though (did that one season and am not inclined to do it again). Speed vs Comfort is kind of subjective. My last bike had a pretty aggressive geometry and my back started hurting, but I don't know if I would have the same problem on a new bike. I'm kind of looking all over right now to see what feels good.
Mark