I haven't bought more than one pair of shoes at a time, though I like the idea in principle. It's just that whenever I get new shoes I find them uncomfortable for some time, and so I don't want to buy another pair of the same type. I don't think shoes are getting worse in absolute terms (though they might be, most things do). I think it's just that shoes are only comfortable for me when they're old - and by that time they've stopped making that type and it's too late for me to stock up. And it's hard to know how long a pair of shoes are going to last until they're out of production.
I had a pair of boots that were some snazzy brand - "Caterpillar" - which I got for half price - £70, and I thought that was extortionate. They were good for just under 3 years but when they needed re-heeling the cobbler said he'd have to send them to the makers and it would cost a lot, so I got a new pair of very ordinary ones, cheaper than the half-price Caterpillars, and they lasted 5 years.
I think I might like buying shoes more if not for the fact that it's so hard to know how they'll feel when I've broken them in. They presumably wouldn't let me walk around outside in them to even get a glimpse of what they're like under real-world conditions, so I have to judge them by walking around the shoe shop. So I don't know how anybody arrives at a good decision, and they're not cheap, so the whole business seems a precarious mess to me, and I don't like buying them, and I wait till they're collapsing before I do it.
I quite like the principle of wearing nice-looking shoes, but somehow it's become a very low-priority thing with me, and comfort always wins over style unless I'm unlucky enough to have to impress somebody at an interview or whatever, and I'm very glad to say that doesn't happen to me much. I don't like spending my time tying shoelaces but elastic sides never seem to have the right tightness (I feel uncomfortable if my shoes are either too slack or too tight), and I don't like those modern shoes that have Velcro to tighten them, though I can appreciate the practical advantage.