> the web site [..] is routinely offered as a fun toy for a new executive to make their mark on to show how they've got exciting new visions for the company
To be fair to Microsoft, this issue affects a great many other companies, even outside the technology space.
My personal favourite has got to be www.britishairways.com, where you can discover older and older versions of their website layered like the concentric rings of some ancient tree.
https://www.britishairways.com/travel/home/public/en_gb/
https://www.britishairways.com/travel/webforms/public/en_gb?...
and even the gloriously broken