Apple did something like this with A/UX back in the day (their variant of Unix which apple sold for its 68k machines). https://en.wikipedia.org/wiki/A/UX The tool that did this was called Commando; I'm not sure if it was hand-crafted, or automatic.

A huge part of the problem is that `man` pages really are only softly standardized, and just, commandline options in general are just softly standardized. They don't all obey the same rules for spaces, capitalization, usage of dashes, etc - they're close, but it's far from consistent.

What we ought to have done at some point, would have been to rebuild the whole suite of commandline utils - to make them all do an ironclad standard, and probably even make them all spit out a totally normalized data format like JSON, man pages included, so that external tools could be built around them way easier without everyone having to write their own parser (or - having to write a generalized parser with tons of 'special-case exemptions' for all the CLI tools that break the rules).

There have been several attempts, but nobody's been willing to do the big "rip off the bandaid" and take the pain of breaking legacy scripts.

We have had automated GUIs generated for command line utilities since PowerShell 2:

    PS C:\> show-command get-childitem

will popup a GUI form for all the options get-childitem takes. It's basically useless because it's a dump of all available parameters. At least they're in alphabetical order, but there's no hint which ones you might want or not want.

Not sure it'd be trivial unless the documentation is really good. I have, however, seen TCL used to good effect of GUIfying a CLI, and providing a scriptable interface so that you can access features that don't translate well to the GUI or (for whatever reason) haven't been made directly accessible in the GUI.