Re Shoes/Shoe Covers:
I don't like the idea of waterproof shoes in this case. Water will still run down your leg, soak your sock and get into your shoe that way. I also question breathability so I don't know if I would want to wear them regularly and don't want to switch shoes for weather. Instead I prefer shoe covers, but NOT neoprene. I don't understand neoprene shoe covers, neoprene is designed to keep you warm when wet, like wetsuit, not for waterproof. Get a set of REAL waterproof shoe covers, not neoprene. I got the Endura Luminite II overshoe -
Endura products - Luminite II Overshoe - E0107
I have a size 45 or 46 and I think I have an XL that fits great. As a bonus, the reflective material on them is great in the dark. I highly recommend these. The other brand I would look at for waterproof is Gore bike wear.