I come to the boot question from a different angle.
If you have well developed and toughened joints and ligaments from years of running, then you'll be fine with shoes. But from an Army, 'carrying very heavy weights over long distances when you're really tired' point of view, you'll want decent and strong boots every time. Otherwise you'll be left on the hills with a sprained ankle or a broken leg. Getting used to such boots also takes many years, so if you don't need to, then I agree, you don't have to.
I forgot to add 'at night and in foul weather'. I like being in the hills in a pair of fell shoes, but they really are fair weather gear for when you know you'll be tucked up in a warm bed in the next 36 hours or so.
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