While this is interesting, I will probably find this too much of work to type in all the stuff again with examples. Throwing a not-so-random extension idea - may be a tool to go through the weird commands in my bash history and suggest me to explain the commands which I just used?

Right now, I usually grep the man pages to search for things relevant to specific context. Something like,

    man find | grep -i --color=always -C10 "file name"

Worked well in most cases. So, for figuring out how to send a POST request, I would try

    man curl | grep -C10 --color=always POST

If that bombs, I would then immediately try

    curl --help | grep --color=always POST

If I end up using certain set of flags frequently, I will set up a bash command like most others. Or, make a weird joke out of the flags, for example,

    ls -lionshit