On the winter issue, consider getting a pair of snowshoes. I keep a pair in my truck for the winter in case I find myself needing to walk a long distance on an unplowed road, or if I have to go offroad. Otherwise think about how you will keep your hands, feet and ears warm. Take care of those three areas and the rest of the body will likely take care of itself. Most so called winter gloves and boots made for the masses will not keep you hands or feet warm for long. You need stuff designed for being outdoors all day. For normal cold I just use the hood that goes with my Carhartt winter weight jacket. For really cold weather I switch to a Mad Bomber Hat which really does the trick on even the coldest days.