> Are you saying you actually want to save "Book draft 1.docx" and "Book Draft 1.docx" as two separate files?
That's a situation where sensitivity can cause difficulty, yes, but for me personally, that's a minor confusion that is easy to avoid or correct. Everything is a tradeoff, and for me, putting up with that annoyance is well worth the benefits of case sensitivity.
I do totally understand that others will have different tradeoffs that fit them better. I'm not taking away from that at all. But saying "case sensitivity is undesirable" in a broad sense is no more accurate than saying "case sensitivity is desirable" in a broad sense.
Personally, I think the ideal tradeoff is for the filesystem to be case sensitive, but have the user interfaces to that file system be able to make everything behave as case-insensitive if that's what the user prefers.
If your goal is super easy filename generation then you're probably not going to leave ASCII.
And if you do go beyond ASCII for filename packing/generating, then you should instead use many thousands of CJK characters that don't have any concept of case at all. Bypass the question of case sensitivity entirely.
A filesystem not being case sensitive isn't a dealbreaker or anything. I just prefer case sensitivity because it increases flexibility and readability for me, and has no downsides that I consider significant.
Not sure why what Windows does is relevant to this, honestly. Personally, I strongly prefer case sensitivity with filenames, but the lack of it isn't a dealbreaker or anything.