Bill definitely wouldn't approve of the current Windows quality. This email by him (2003) is very interesting. It looks like he was powerless to stop the degradation.
The guy's still a narcissistic asshole and likely sexual predator, but when even Bill Gates says the UI sucks on Microsoft products, you know the rot runs deep.
Definitely a wild read. Bill has a certain style of writing; here is my favorite part:
> So I gave up and sent mail to Amir saying - where is
> this Moviemaker download? Does it exist?
>
> So they told me that using the download page to
> download something was not something they anticipated.
>
> They told me to go to the main page search button
> and type movie maker (not moviemaker!).
>
> I tried that. The site was pathetically slow but after
> 6 seconds of waiting up it came.
>
> I thought for sure now I would see a button to just go
> do the download.
>
> In fact it is more like a puzzle that you get to
> solve. It told me to go to Windows Update and do a
> bunch of incantations.