1. Rough side out.
3. My leather shoes never shrank length wise. But leather sole for outdoors is an extremely bad choice; it doesn't keep your shoes dry. Hand welted (or gyw) construction is really bad in keeping feet dry as well. But if you are silly enough to believe in them, beware of trench foot.
4. did you ask for half or full sole?
Thank you for your answers! Very helpful.
May I ask why rough out? So pure cement/glue construction is best for keeping the water out? A lot of the rugged boots involve some type of stitched construction with plenty of cement, as far as I can tell. One example would be a boot with a leather midsole and a Vibram Christy sole cemented/glued to the bottom of that...
I simply asked for them to be "resoled," and assumed that would mean a full, new sole. Perhaps that was a bad assumption on my part.