What's something about the web that's obviously broken?

I'll start: No version control history and all the content is dynamic.

Hyperlinks aren't natively bi-directional.

You can't add annotations (read/write/add behavior) to websites you don't manage.

No interoperable permission system spanning websites (e.g. WebDAV)

Pretty much no website is interoperable (beyond speaking e.g. "http" and "json").

XMPP is dead.

Entire business model of orgs like Zapier is piece-wise integration of disparate cluster- of web services. Worth hundreds of millions.

Even though a lot of the "journalism" is terrible non-journalism, it's still pay-walled and laden with advertisements.

When a web service goes down, we ask other people on twitter for confirmation.

Link rot. If you link to a website, chances are it will change or die within 100 days so you're basically wasting your time citing anything.

Very few browsers have any reasonable mode for auto-caching websites you visit for offline.

Look, if I visit a web page once, I want it literally forever. And I want all its links archived too (because spacial & temporal locality: I'm likely to revisit a thing & things nearby)

Passwords. Why do I need 100 passwords or some paid password management service when my operating system is already a password management system which is capable of running federated, socketed services.

Google maps? Yeah, sure alright. I take it back, google maps is practically perfect, bless your heart.

But, besides google maps, what has the web every given us...

Of course there's Wikipedia, Wikidata, Khan Academy, Craigslist, EFF, irc, Internet Archive, github, stackoverflow, Panlex... Well alright, sure, the web did give us those...