I have never had a pair of shoes that could last more than a few years. I’ve even paid for expensive shoes that claimed to be super durable and they fell apart faster than a cheap ass $10 pair from Walmart.
I’m at a point where I have very little hope that anyone, anyone, makes good, comfortable shoes that aren’t made of paper mache.
You save in the long run in terms of build quality, comfort, and arguably most importantly economics. Going with Pacific Northwest (PNW) style boots with high quality lasts (the “frame” a shoe is built upon), all leather construction, Goodyear welting, etc, will mean the shoe is going to be more supportive to your lower back and arches, leading to less pain and joint damage down the road.
And while resoling is not free, it’s certainly not super expensive either. I see cobblers offering to restitch a new lug onto a pair of boots for as low as $60, which is still cheaper than going with anything other than Walmart-tier schlock, plus that resoled boot will last at least another 2-5 years, depending on wear.
I do a lot of light hiking, probably putting a good 25-30 miles on my boots every week, and they’ve held up for multiple years of use.
$60 is still pricy enough that it’s probably worth it to just learn how to resole boots by hand.
I can’t imagine you would need much equipment for it, although I’ve only resoled leather sandals and those just needed shoe adhesive, a leatherworking needle, and some heavy-duty nylon thread.
I watch some artisan videos on youtube and there’s a shit load of skill and tools you’d need. $60 would be more than fair