A pair of shoes could last about 6 months of everyday use, with an average of two minor repairs over that period. Among these "minor repairs" are repairing broken stiches, reattaching uppers, and patching those areas where the leather has worn through on the upper or sole.
Eventually there comes a point when the sole has worn completely through. Historically, replacement of the sole was a constant necessity.
Shoes can be made reasonably waterproof, although not watertight, by means of oiling them, or rubbing them down with tallow or lard (modern shoe polishes are often a form of paste wax that serves this function). However, unlike many modern treatments, the use of which is really up to the recreator, and just how authentic they want their shoes, these are not a "one shot" application. Shoes need to be regularly looked after, re-waxed or tallowed every so often (as much as every time you use them) if you want them to remain even reasonably wearable and water-resistant. This may seem labor intensive, but no more so than a soldier keeping his or her boots polished in the field, and with the reasons more clearly explained. You may wish to avoid things like Crisco as they will wash away and leave the leather stiff and brittle, since purportedly, as "Shortening" they cause the collagen fibers to shrink (I don't know that this is true, since I've never tested it). If you feel you HAVE to use something like silicon, that's your business, but remember it's not authentic; but then again, I can't prove that regular applications of tallow or wax *are* (although my wife keeps reminding me that there is a chapter in Farmer Boy, one of the "Little House" books by Laura Ingalls Wilder, that describes this process being used on moccasins during the 19th century.
To be worn comfortably, the shoes should be worn in an authentic manner, which can mean wearing woolen socks and stuffing the bottom of the shoe with straw or wool, moss or hair since it is alleged that straw and wool will retain heat when wet, and this can be important during the winter.
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Footwear of the Middle Ages - Wearing, by I. Marc Carlson. Copyright 1996
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