I try not to tour in the rain. Although, I've had plenty of wet days for commuting. Either get wet in the winter around here, or don't ride.

For summer riding, I just have some Tennis Shoe style SPD shoes. My Specialized shoes are heavy, hot, and flexy, so no tours. My Lake shoes are light, and I think even have bottom ventilation. I've had them for a few century rides, but not overnight yet. The Shimano casual SPD shoes are pretty good, and comfy.

For the winter, I have some neoprene Shimano MW-02 (precursor to MW-81) shoes. They're about worn out, so I'll probably be going to the replacements soon. But, they are Comfy, and can get pretty drenched, and still feel comfy. they do take a bit to completely dry though. I rarely put them back on wet though.

My longest recent tour was 4 days (I had planned for 3, but didn't quite make it). I think I probably brought a couple of extra pairs of socks. They're light and easy to pack. I had a washcloth that I just hung on the outside of my bag. Anyway, thinking about longer trips, and will probably have a pot dedicated to washing clothes and socks. Then just hang them to the outside of the panniers to dry. Hopefully bone dry before needing them again.

I haven't been using a lot of wool. Mainly synthetics which don't hold the moisture as much.