I'm not sure it's related to the CL workflow, but in a recent project I had to compare the output of different runs of a program. (Run it, make a few tweeks in the definitions panel, run it again, fix something, run it again, ...) I wanted to compare the outputs and sometimes to copy&paste parts of them later.
It would be nice that DrRacket has an option to not erase the previous output like Python's IDLE (see /drracket/issues/671). I agree that it can be confused for beginers, so I'd not enable it by default.