I start each fall a bit grumpy and sad because the chilly, wet, shorter days initially uncomfortable. But pretty soon I'm putting on an extra layer and a wind breaker and the weather is less of a bother.
Then there is the darkness. My lights are better for others to notice my bike at night but not good at all at lighting the road. I'm ordering a new light later this week.
My other weather challenge is getting a set of studded tires. The LBS has tried talking me out of riding with studded tires, saying that the roads are cleared and salted. But only the main roads are cleared first. The side streets I ride on are plowed and salted days later, or in the case of the street I live on, not at all. Then in between the snow falls, it'll rain, then freeze, and the world turns into a rough skating rink.
Regardless of the different challenges, it's still much better riding my bike during the dark, cold, rainy, snowy weather than standing at the bus stop waiting for a bus that is 30 minutes late.