"I don't know about all of the other reserved characters, but the colon is the path-separator character in classic Macintosh APIs and I doubt they would have ever been able to "fix" that."The fundamental issues is that users should be able to type any characters including colons that appear in day-to-day use, whether it be a book title, report name, movie title or whatever without ever having to worry about it.
The fact that they cannot do so and that they deliberately have to transcribe a name to another or shorten it to accommodate an operating system's limitations wastes time and leads to errors and confusion (anyone who has ever run an IT help desk in a large organization knows this).
I'm aware of the Win 10 'long paths' fix and I've also seen the registry patch which some suggest possibly fixes earlier versions of Win 10 (I've not tried the patch). That said, the filename length limitations remains a problem for two reasons - the filename is still too short and that many programs are likely to crash if filenames were to exceed 255 chr$ (as they'd be unaware of it). To overcome this, the operating system would have to also present a shortened 255-character filename to the program in the fashion it did back in the early days for programs that only understood 8 * 3 filenames. As I see it, it's only a halfhearted too-little-too-late tweak and the job needs to be done properly.
"My number one peeve for a long time was "Documents and Settings" instead of "Users" on Windows XP..."
This is still a problem, in fact it's a real pain. Right, D&S was a pain but so too is 'Users' and 'ProgramData', both should be completely movable even to the extent of having them work from a USB stick. Whenever I set up Windows it takes me days to configure my programs so as they dump their data/save files to specific locations on other drives (this makes transferring data to Linux etc. much easier and it's much safer too if files can be kept in locations where they aren't expected to be found). In fact, this should apply to all user info including users' program files. As I see it, these limitations are just bloody-mindedness on Microsoft's part (where the user isn't an administrator, the administrator would be able to still lock user directories and files to suit the local policy).
Yes, there was an excuse for the problem 20-30 years ago but not nowadays. Unfortunately, this is a 'mindset' problem of programmers. They're so used to acronyms and shortening things that they don't realize or care that ordinary users do not understand why they just cannot type anything as they did on typewriters (and something I've not yet mentioned: why they cannot type between already-typed lines or within margins, as the old-timers continually claim they once could do with ease but can no longer do so).