Is he walking his way through the soles, or is it the uppers that go first? With soles longevity and comfort are always a trade off, regardless of cost. I've always found the MIE Dr Marten shoes to be very well made, certainly better than the boots, and should be good for a year (that's how long they lasted when I was a boy, we'd kick the shine out of them though, as kids do) They'll hurt like hell until broken in though.