Well I'm not going to pretend all of Microsoft's efforts have gone into being progressively more sleazy, just most of them. 2009 is the year Windows 7 released.
The idea is that Windows 7 was the last release without network-sniffing, privacy-intruding malware (at least, as it came stock from Microsoft, which it did not when preinstalled on a typical PC).
For me it seemed that with Windows 11, Microsoft was attempting to recreate the hypetrain they'd built for Windows 95 -- but without the groundbreaking improvements over the previous version of Windows that Windows 95 had. And the result was just desperate and sad.