So to preface: I don't use any web functionality in password managers at all, only the client applications. But that's the context for my regret over the forced subs too.

>I can't think of any other class of product where timely updates from the developers are so critical to the utility of the product.

I can think of a ton actually, although I guess it depends on what you consider important functionality there. Now, there is ongoing maintenance needed for things like keeping up with browser integration, but I'm not sure exactly what security updates should ever be needed unless they really fucked something basic up. The only things that need constant attention are their own cloud service, but that's a function of it being their own cloud service vs someone running their own server or syncing via Dropbox.

>You could even argue that an unpatched, out of date password manager is worse than no password manager.

I don't think you could frankly. Like, what's the threat model here when we're talking data that lives on our own systems and is E2EE? Fundamentally, password managers do not defend against the trusted end point being pwned, for that you need an HSM of some sort (or at least some weaker but still somewhat functional kinda of 2FA). All data from the end system should be fully encrypted before leaving, and since the system is trusted by definition timing attacks shouldn't be a concern (or at least are trivial here to negate entirely), so the security should depend purely upon the PM's ability to perform basic at rest crypto, use a decent key stretching as needed, etc. Which is frankly a solved problem with well vetted free libraries, that's not the hard part of security.

Honestly, 1Password and the like aren't that different from the macOS Keychain Access I'd been using for many many years before hand. They've got better organization and UX flow these days, and browser integration is a genuinely big deal. But I never had any problems with Dropbox sync with pre-1P.com nor do I still have any problems with sync there. In principle, the 1P team could have made all the admittedly alright group stuff and so on available as a standalone server thing people could run along with their own cloud offering of the same, similar to the way Gitlab and many others do. Buy the server/client licenses standalone and run infra yourself, or not, your call. WiFi sync didn't have to be left as primitive as it has been either. Etc. It's a business decision for them to push subs because subs are very profitable. And I recognize yeah, it's a way to make lots more money in a reliable fashion which people like. But I still regret the sub trend and think it's usually a negative overall particularly for people trying to fill situations outside the norm. 1Password's sub thing for example doesn't scale with large families, there is a huge disconnect between a small family and an "organization" in their pricing and general structure which isn't due to cost basis, it's due to their perceived ability to pay.

I'm genuinely optimistic though that things like Webauthn represent real turning points, and we're finally (10-15 years late but better late then never) moving away from the madness of service passwords and managers "have i been pwned" and all the layers that essentially recreate PKI, very badly. As far as security goes, neither I nor anyone else should need to give a single shit or change anything at all if a website is completely utterly hacked, because the only authentication that should be there should be a public cert for me. Damn it, asymmetric credentials was solved forever ago!