Nushell has a SQLite history mode which captures more metadata than is typical. I haven't looked into extending it, but it seems like a good setup for adding enough so that some of these cognitive requirements could be recovered from history rather than thought of up front.

Like if I tend to go down the wrong path, fix it, and then go down the right path, maybe that's a pattern that can be identified and then when I search history it finds two or three commands which together set me on the right path in the first place.

I mean, thinking ahead is always gonna be better, but I don't always.