alt Hacker NewsThe web was not fine.
If you wanted to accomplish anything more substantial than reading static content (like an email client that beeps when you get an important email, or a chat app that shows you new messages as they come in), you needed to install a desktop app. That required you to be on the same OS that the app developer supported (goodbye Linux on the desktop), as well as to trust the dev a lot more.
We seem to have collectively forgotten the trauma of freeware. Operating an installer in the mid 2000s was much like walking through a minefield; one wrong move, and your computer was infected with crapware that kept changing your home page and search engine. It wasn't just shady apps, mainstream software (I definitely remember uTorrent and Skype doing this) was also guilty. Even updates weren't safe.
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Somehow we have cross platform software today that isn't Electron slop. And shoehorning absolutely everything into what used to be a document oriented application, creating this grotesque mutant abomination we have today, has just moved the minefield. How many RCE's has Chromium had?
Also, up until Windows Vista, Microsoft thought that making every account on their OS root by default was an amazing idea, further exacerbating the problem you describe, which I don't deny existed. Software distribution on Windows is still a shit-show today, but I guess there's too much momentum to move to a Linux-style repository. The Microsoft Store is a piss poor attempt.
I use a desktop mail client. I have always used desktop applications. I have never had any desire to use web mail clients. Likewise for office suite applications. A true desktop spreadsheet, word processor, and slide deck are always superior.
The web as an application platform has always been a half-baked, second class, inferior experience for the user. It has always been about developer convenience at the expense of the user. No thank you!