>Can I suggest thrifting

Thank you for suggesting this! No idea why it never crossed my mind to for shoes at a thrift store; I've had ridiculously good luck in the past with coats and jackets before. Turns out my luck is holding - I went to a few near me and did not find boots, but I did find these for $17. Even including the $85 resole (which they needed; the soles are worn down almost all the way to the leather), that's still a hell of a lot less than I'd pay new for something comparable in appearance and much lower quality. The leather's in great shape, these seem like they should last a while. Plenty of time to save up!