My outer soles tend to die within two years or so, but I managed to find (hiking) shoes that can be resoled - we'll see how that goes.
I also figured out ridiculously late that there's such a thing as shoe width, and I needed wider ones (though leather can also stretch a bit).
Another pro tip: walk for about an hour before trying on new shoes, as your feet expand once warmed up. By the time you find out you've used them outdoors too much to return.
