I can offer only a few experiences, most of them tangential to your question:
1. When I was a kid I lived in snow country. My mittens would regularly get soaked from handling snow so my parents got me a pair of waterproof ones. It looked like a great idea on paper but they turned out to be just awful. They didn't have much insulating value to begin with and they'd quickly get cold and clammy inside from condensation.
2. Nowadays I hike mostly in warm-to-hot conditions so I choose all my "normal hiking" shoes for good ventilation. I do have a couple of pairs of Gore-Tex-lined waterproofs for when I expect to be dodging puddles and stuff. One time the forecast was threatening rain so I spent the day hiking in the Gore-tex shoes. I rarely get blisters but that day I was surprised to end up with a blister on the bottom of one toe. When I read up on the subject, I found out that damp skin is more likely to blister than dry skin.
3. I was in Yosemite Valley in January, just to try out my snowshoes and other gear and see what the park looked like with some serious snow on the ground. I'd prepared for the occasion by buying a pair of Merrell Moab Waterproof Mids at least one size bigger than I usually wear. I wore them with double socks, "hiking" weight inside "expedition" weight. That combination turned out to fit quite well, and my feet stayed warm and dry the whole time.
