This article took me down memory lane. Windows ME was what got me to move to Apple. The one I remember that Gates tried to push through, but wasn't able to pull off, was after they'd wrecked Mozilla, they tried to sneak "smart tags" into Internet Explorer. The backlash was so extreme, they backed off.
For those who don't know, smart tags would be embedded in the browser, and would automatically convert key words to clickable links to Microsoft partners (paid advertisers.) So, if you ran a blog on digital cameras, and Nikon was a Microsoft partner, every time you used the word "camera" in your blog, Internet Explorer would make the word a clickable link to Nikon. Your site would become an advertising platform for Microsoft, and you would not get paid.
I remember Wordperfect and Lotus 1-2-3 would start crashing every time I did a Windows update. Read a few articles that the owners said MS would put out coding guidelines then break the guidelines with their own products, but not notify anyone that they were changing the coding.
One of the dirtiest tricks in the Microsoft Book of Dirty Tricks.
As a developer whose applications and utilities had to run on Windows, that crap made me furious.
I grew sick and tired of Windows breaking stuff for no apparent reason other than Microsoft not being honest.
It's one of the main reasons I primarily use Linux and MacOS these days, and go into a Windows VM only for those tools that only run on Windows, or to test a cross-platform application on Windows. And hoping to God it doesn't fetch up against yet another place where Microsoft lied or screwed up. It's really freakin' annoying.
It could have been so much better.
Personally I don't blame Gates as much as Steve Ballmer. That man did more damage to Microsoft, and everything around it, than you can imagine.