TLDR Its 100% worth it

I literally made this same transition in my footwear / clothing approach. r/goodyearwelt is your best friend

Did my research and I invested in a pair of Redwing Iron Rangers ~$350ish. An American classic that ages well and is considered well built and good quality. 2 years later of wearing them literally daily (90% of the days at least) , they continue to look good as new. My only complaint is my tread and traction is worn down after 2 years, so they are a bit slippery in the snow (more on that later)

For upkeep and maintenance, it sounds daunting but is really very simple. Rose Anvil has some good walkthroughs. Kiwi Saddle soap with a dauber (small) brush ~$15 total acts as your cleaner. Some leather conditioner (I use cobblers choice) with a bigger brush ~$40 is your treatment/waterproofing. Shoe polish or wax is really optional. I do my boots once every 6months. Step 1 - Knock off any loose mud/debris, Step 2 - Spray the boots with distilled water and Scrub them with the lathered up saddle soap, Step 3 - wipe them clean with a clean rag and let them dry for ~24hrs. Step 4 apply some conditioner to the boots, either with your fingers or put some on the big brush and start doing some passes (think of it like lotion on your skin, enough to moisturize but not too much where it becomes overloaded and oily) Step 5 let them rest and dry for another ~24 hrs, just so the conditioner soaks its way in evenly.

FYI The conditioner is your weather protection and healing lotion. It doesn't completely waterproof the boots, but it greatly helps shed water on normal levels (walking through puddles, rain, snow etc) The only way my feet will get wet is if I stand in a river for a full 30 seconds. To completely waterproof leather boots you need wax or snowseal, and neither of those are particularly good for the leather's longterm health

All that being said, I am never going back to daily cheap shoes. Once the boots break in and form to your foot, nothing is more comfortable or feels as natural. Technically yes you should give your boots a break to breathe and fully dry out with cedar shoe trees, but I think of that more as a rule for the Vibergs and bespoke builds of the leather world, where more emphasis is placed on the finer details. Like I said, daily wear and my boots are doing excellent. A big part of that is the leather type as well, do your research into vegtan vs cromexel vs roughout vs cordovan etc, and pick the one that has the qualities that fit your lifestyle (or looks the best lol).

My solution for my treads becoming a little slick in winter...I ordered a pair of Nicks boots to act as my "winter set" and my Redwings will be my lighter "summer" boots. This is where cost vs quality starts to play a role. Again Rose Anvil does deep dives into the boot construction and quality, and you will see why Redwing and Thursdays are ~$300 and Nicks and other PNW boots are ~$600. You can usually see a direct relationship in the amount of material and leather and build quality that goes into a boot vs the cost. Stick to reputable and pedigree brands, and you will absolutely get what you pay for.

Hit me up if you have any questions