You can solve your shoe problem with a temp fix. Use a thin plastic bag. Cut it off so it doesnt stick out too high over the shoe. punch some hole in for ventillation (unless its raining).
Best worn between 2 pairs of thin woolen socks.
At 40F/4C I would use a neck warmer pulled high , but probably not over my mouth unless Im doing a cold descent. You need to let the moisture escape