My Windows 10 updates had been failing for the past 6 months. When shutting down my PC I'd get the notification to "update and shut down", but the update would routinely fail. I thought the outstanding updates were the reason I wasn't given an option to update in place to Windows 11, but that was actually because my i7 7700k isn't officially supported. I ended up needing to create a Windows 11 iso that doesn't enforce hardware requirements with Rufus [0]. I was building a new gaming rig in tandem, so I reformatted the lone remaining SSD on the machine and left the new windows install unactivated as I plan to give it to a neighbor or family friend who can be tasked with buying a copy of windows. But this means I was left without any free Windows 10 -> 11 upgrade and had to buy a new license for the new rig. I didn't try to do anything other than browse the internet on the unsupported hardware, but things seem fine.
So far Windows 11 on the new rig has been very smooth/stable and I can't think of any issues I've had after 2 weeks of gaming and other typical use. But the amount of internet-driven widgets that ultimately are a medium for ads is frustrating.
I have the same reaction as you - his persona makes me physically uncomfortable and I feel bad for the artists unless they have the common wholesome reaction to well-done research.
But how much of it is a "shtick"? I take it the guy is just weird. If that's the case, it's not forced or over the top.