In my experience, cold rain is actually easier to dress for than warm rain. I've got a Craft rain jacket that is fantastic in temperatures below 50 F, but it gets too hot once the temps approach 60. So I have a much lighter weight Castelli jacket that I use for warmer rainy days. It is also very small, light-weight and packable so it fits in my seatbag without taking up much space.

I don't mind riding in light rain, or riding on days when the forecast is iffy -- that is, it might rain. However, if it's raining hard or steady, I'm gonna drive most of the time. The exception is during periods when I've missed a lot of rides due to weather or other factors and I just want to get some miles in. Otherwise, I dislike riding in the rain. I hate not being able to see due to my glasses getting all spotted up and foggy. More that anything, I hate having to clean my bike later. It's not worth having to spend 30 minutes cleaning my wheels just to ride in the rain. Most of my rain rides come on days when afternoon thunderstorms pop up, or the forecast called for a 30% chance of rain and it became 100%, or unexpected showers develop. If it's raining in the morning, I will usually drive that day unless it's a light rain and expected to clear during the day.