I think the best way t o think of the scenario is the neoprene should be off the foot, not on the foot. It should be over the shoe. That way you get a double benefit from wearing the wool socks which help keep the feet warm and then you have both a heat and wind barrier on the outside of the shoe which furthers helps to keep the feet warm and protected. If you have decent booties you should be able to keep them for multiple winters. My first couple pair of booties only got me one winter of riding a piece. My most recent one, which I'm now using for my fourth winter have been quite nice. The zippers blow out on them generally in the first winter, plan on that happening. Its not what is behind the foot that matters, but what is in on top of and in front of the foot that matters. My booties all ripped up nicely but they are still functionally quite nicely, even over Thanksgiving when the temps were only in the lower teens for highs my feet were still comfortable.