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People might do that, or not... but the fact that someone had to impose these restrictions in the first place, to me, is a warning sign that many places inside the respective software will have parsing issues/issues with handling of "weird" filenames.

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In many cases, the restrictions come down to the underlying file-system and how it works. Not saying it is right or wrong, only that the reasons can be very fundamental.

I think that's a fair point if you're talking about a disk that's attached to a computer. Yes, the file system on the disk restricts what you can do.

For a cloud file synchronization app, though, I'd expect Microsoft to not let these kinds of restrictions leak down to clients.

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