One problem with waterproof boots is they do not let your feet breath... I know: seem obvious. If you were hiking in warmer weather with insulated waterproof boots were the boots leaking or were your feet sweating?

I am a few years removed, but when I was a kid I spent quite a bit of time outdoors in the snow including snowshoe backpacking, hunting, and cutting firewood. We would often get a bit of dampness in our feet from sweating while active. For rubberized boots a small hole usually only became apparent when standing in puddles and walking through slush. Waterproofed fabric that lost its integrity could absorb water and become a bigger and bigger issue the longer you were out.

The bigger issue than holes was snow working its way in from the top. A good pair gators was a must in deep snow. For boots we usually bought cheap Sorels at k-mart with the liner you could pull out and dry.