Some shoes are able to be resoled/rebuilt by a cobbler when they wear down, but they have a more complex/handcrafted construction which means their price tag is higher, and of course it's not free to have them resoled, so you don't automatically save money by going this route.
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
I had a similar problem. I bought a pair of White's boots. Hand made and stitched in Washington. Able to have the soles rebuilt. For 3 years with daily use they are still in great shape. I love them so much that I bought a second pair .
I have a pair of Finn comfort shoes that have lasted 20 years. They are well designed to easily have repairs such as resoling, replacement of the cork footed, or other wear points. And they are super comfortable
Sounds like you're looking for boots, not shoes. I hear you, I hate how I can rarely find a good pair of shoes and then when I finally do, they wear out in 1-2 years and anything remotely similar to them has been discontinued. I hate walking through a snowbank in winter and having it get wedged around my ankles. I hate stepping in a puddle and it turns out it's deeper than expected and your feet get soaked. Fuck shoes.
Several years ago I got a pair of Redwing 4473 boots with the zipper insert (I'm too lazy to mess with all those laces) and they're still my primary work boots. I just had them resoled for the 2nd time and they're in excellent shape again. Awhile back I realized that they were by far the most durable, comfortable, and all around best pieces of footwear I've ever worn in my life despite a complete absence of cushioning, gel insoles, foam padding, etc. So I ditched shoes altogether and just wear work boots that can be resoled. I just don't wear the nicer pair when I'm painting, digging, mowing, etc.
They don't make the 4473 anymore and I heard the overall quality has gone downhill but I think you still need to research the individual boot model as much as the maker because some are winners and others are lemons. For my nice not-work boots I'm trying out the Solovair crazy horse gaucho 11 eye derby boot. A local cobbler installed a side zip on them for me for $70 because again, I'm lazy and don't like to screw with boot laces. I won't know whether they're worth it or not for a few more years but I like how they look and they've been comfy enough so far. Pair some good leather goodyear welted boots that are properly broken in with a pair of wool Darn Tough socks and you'll never go back.
I am a fan of Thursday Boot Company. I bought a pair of Captain's Boots from them a while back and they are my favorite boots. I basically looked up leather nerds in forums and found a positive review for them - they have an in-house leather production thing going where it is kind of like a more expensive boot for less. They still cost like $200 but apparently the quality is up there with a five hundred dollar pair. Either way I usually buy really cheap shoes from payless so I don't have a lot of experience to compare, but they fit like a glove and are super comfortable.
KEEN replaces your worn out shoes for free, or so I've heard. They aren't my favorite for comfort or style, so I haven't taken them up on it.
You may be thinking winter shoes, but I have had a great experience with Rainbow sandals. The first pair lasted me 10 years, wearing every summer (which is almost 6 months here in Austin).
For practical, durable and quality made products that are made to last.