I no longer upgrade most devices. I have become a Never New'd.
Device and software makers cannot be trusted, and it only ever gets worse. I have become a luddite who still uses stock Android 8.0.0 on a rooted Samsung phone. It works perfectly, so why should I upgrade? I've seen the newer versions of Android - the notifications system is worse and it adds no new features worth mentioning. Samsung's own fork of Android is a horror-show of bullshit. I turned off auto-update in the app store because the applications only ever seem to get worse, usually when someone decides they need a UI refresh, which is every month. My banking apps would sometimes update and then tell me I could no longer use them because I have a rooted phone, so now I just don't upgrade them, and it works fine.
It's not just phones: I refuse to upgrade my networking hardware too unless there's a critical security flaw. Every version of the Ubiquiti Unifi Controller past 5.9 is a hot mess, with the latest one introducing adverts, of all things. My EdgeSwitch/Router gear is similarly left at whatever the last working version was until I need to upgrade for security, and then I make the most minor upgrade possible because the newer firmwares inevitably break everything. I've just returned a new Unifi Flex PoE switch because it involves upgrading and I cannot risk my network falling over when we work from home every day. Every new release of their firmware or controller comes with reports of it killing entire networks.
Open-source isn't immune to this. Ubuntu upgrades have always historically been a 50/50 chance of everything imploding. Is it as bad nowadays? I dunno, I install an LTS release and then install the latest LTS release 5 years later when I replace the computer. It's not worth the hassle. "Something something Arch", you say, but then that just provides the upgrade pain like a million tiny papercuts every day.
I'm a software engineer and certifiably grumpy, but it's not just me - tech companies are losing the trust of users all over the place. I talk to plenty of "normies" who are sick of updates changing everything but giving them nothing in return. Like Apple changing the behaviour of message backups when introducing iCloud or other assorted bollocks like that.
It only ever gets worse.
Is there a way forward? Or an alternative path?
It's fairly telling that pretty much all my major pain points come from software/firmware/devices developed by companies. At the end of the day, they don't have your best interests at heart - public companies are beholden to their shareholders, and your experience ultimately doesn't matter because there are apparently an infinite number of alternative customers.
There are very few tech companies right now that I trust implicitly to provide me a pain-free upgrade experience. Valve, perhaps? I've been using Steam for 16 years and it has never broken for me, across any OS. And it continues to get better, with amazing support for Linux. I can't think of another company whose product I have used every day for that long and not grown to hate.
I have more faith in open-source projects. I am gradually replacing pretty much everything in my life with open-source software, and I'd like to be able to replace all my hardware with open-source hardware too. Endeavours like Pine64 are exciting. We really need more equivalents in the network hardware space.
Open-source software provides an alternative: you can just fork the version you liked, if anything changes. Every GUI change on a distro like Ubuntu results in a new spin-off distro that sports the previous GUI. And that's fine. That's how it should be.
Long live the luddite.