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@lae
Hmm, shame about the Redwings.
I've done a fair bit of walking and backpacking just wearing DMs (most of the south west coast path, Skye, Carneddau) and they were okay. The only real problems are lack of padded collars and severe lack of grip (and the fact that my latest pair fell apart this summer, less than a year old). I think I'm of the persuasion that unless you're doing some serious performance hiking, specific hiking shoes aren't essential (although they are, of course, preferable if you have the money, which I don't).
At the moment I'm thinking that the best course of action is to buy some boots above and see how I get on with them - if the walking is serious enough to warrant a pair of specific hiking shoes, then I'll get some - or in other words, I definitely need some normal boots whereas I only possibly need some hiking boots.
The Timberlands were my favourite option until I found out that they're not welted, they're glued. edit - actually I'm unsure if they're welted or not. They're not listed as welted, but they look like they are.