

I don’t think you can expect any VPN to work without sign-in for very long. Google’s playing whack-a-mole with VPNs.
I’ve never actually tried signing in with yt-dlp. How easy is it to make a throwaway google account nowadays? Do they require phone verification or something similarly onerous?
Kind of the opposite. It takes more effort to make a filesystem case-insensitive. Binary comparison is the laziest approach. (Note that laziness is a virtue.)
I’m on the fence as to which is better. Putting backwards compatibility aside, there’s a perfectly good case to be made for case-insensitivity being more intuitive to the human user.
Apple got into a strange position when marrying Mac OS (case-insensitive) and NeXTSTEP (case-sensitive). It used to be possible to install OS X on case-sensitive HFS+ but it was never very well supported and I think they axed it somewhere down the road.