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Now I’m wondering how you could create ‘uncomfortable’ versions of simple command line tools (ls, cat, more etc.) or perhaps shells.

Emacs and/or vi, depending on your inclination, have text editors covered already, of course ;-)

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Well, bash offers vi and Emacs as editing modes. We're already covered on that front. Many of the parameters for ls are cryptic, making it awkward to use for anything other than routine tasks without referencing the man page. more is so limited that many people choose to use a program used to concatenation files (cat) as a file viewer. Those who don't want to reach for their mouse to use their terminal's scrollbar buffer will use less, since it does more than more. Don't bother parsing that last sentence with bison, unless you have a yacc to shave.
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jus used new ubuntu instead of ifconfig (weird name) it had ip couldnt figure from the help how to get actually show the ip

so linux is already there

Yeah, Linux has been trending to incomprehensible commands.

In terms of usability, moving to FreeBSD from Linux is quite a positive experience. Pity that hardware and software support is limited on the BSDs.

Feed all command output through AI to summarize the results instead of actually giving the results.

Results from ls would be a few sentences explaining the types of files in the directory. Add a -l on there and it will give you a general overview of the permissions and size of the files. Ex. “These are rather large files that are primarily, but not exclusively, limited to root.”

Results from cat would give a summary of the file. You’d get the same results, with some degree of randomness from more and less as well.

Using any command with sudo would provide the same type of results, but in all caps.

Trying to pipe commands together would be a slop multiplier.

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Use an agent for all CLI work.