So, after like 8 months of dumbphone only, I've given up.
It wasn't one majorly annoying thing, but just a non-stop death by a thousand cuts. Modern life really requires at least possession of one of these stupid little rectangles, and if you don't have one, you get slowly nibbled to death by the ducks of modernity.
So, rather than redouble my efforts to bend the world to dealing with me wanting to be a bit of a luddite weirdo, I've given up and just..... bought an iPhone SE and paired it with an Apple Watch 8 I already had.
See, the thing I really didn't consider is that I pretty much already had the ideal dumbphone: this AW8 is a cellular version.
It does phone calls, text messages, and has sufficient ties to modern services (music, podcasts, audiobooks, maps, etc.) that it is, by itself, a 60% solution. And just for perfect clarity: there's a lot of things wrong with the watch that make it not an ideal device, with the biggest one being really not fantastic battery life.
For everything the watch doesn't do, I also have the phone, but the phone isn't strictly required, and I can simply leave it at home when I don't want to deal with all the modern smartness and just rely on the watch.
For sure, it's not a cheap solution since an iPhone and a cellular watch is a giant investment even if you go for the "cheapest" versions, and I'm paying for two cellular plans (though, with US Mobile it's $96/year for each so, relatively speaking, still pretty cheap).
How do you do TOTP 2fa on a dumb phone? You really can't.
I have to keep two copies of my media library, because the smart devices can play flac, and the dumb devices can't
I also have to keep two copies of my audiobook library: the smart devices play from audiobookshelf, which wants single-file variants, and the dumb devices need to be split into small chunks
Zero access to any of the home automation stuff on the dumb devices
Dumb phones are limited to SMS and MMS, and that dramatically impacts your integration with people on smart devices using iMessage or RCS, and you're basically that guy with the shit that's fucking everything up for everyone else
Calendar sync? Nope.
Contact sync? Also nope.
E-mail? Good luck with that - if you're expecting something important, carry your laptop.
Wifi hotspot? Not on the phone I had, so nevermind about carrying your laptop, won't do you any good.
Voice mail? Sure, but good lord is ye olde dial-a-thing-and-hit-7-wait-no-8-damnit-i-mean-6 voicemail shit. Visual voicemail is 10000% less horrible
Edit: Also:
T9 texting. I kinda got okay again at it but would not say it's preferred anymore
And on and on and on. None of those are dealbreakers on their own, but it's always something that either you can't do, or can't quite do right, or is actively a problem for everyone else you're interacting with and you just.... end up with so many little annoyances you're not sure doing this makes any sense.
i've only ever had 'dumb'phones because the lowest cost is most important to me. everybody's needs are different. your issues with them are all 'non issues' for me.
i just get by as i always have. work and home for the internet (and i'm rarely far from either), a book when i'm out for extended periods instead of doom scrolling at every idle moment, and i don't do any 'personal business' online--at all. about the only thing i 'miss out' on is 'app exclusive' deals at stores and restaurants and things like that. nbd.
i do work on other people's 'smart'phones regularly (software, interoperability, configurations, etc), even though i've never had my own.
if i still lived in the city (haven't in over 20 years), i would probably have a cheap one, though--mainly for transit schedules and such. varying from your daily routine was always a pain with pocket schedules.
I have Audiobookshelf running too, and all of my audiobooks are collections of mp3 files (numbered properly by either Libation or downloaded directly from Libro.fm).
I'm not sure where this "wants single-file variants" comes from.
The Shelf works fine with separate mp3s.
And I love T9 typing so much, I've installed the Type Nine keyboard on my iPhone.
I’m not sure where this “wants single-file variants” comes from.
I was having issues with pirated audiobooks stopping playback, being unable to resume playback, and losing playback status and location all the damn time, though this was a while ago.
The suggestion was to take these random audiobooks and condense them into one file, instead of the 15 tracks per disk, 20 disks per book mess they were, and sure enough that completely fixed the problem.
If it's no longer an issue, cool, but for a while playback from books in lots and lots and lots of parts was flaky as fuck.