So, this is not "bringing it to the 21st century." I feel like what would actually do that is related to the idea of don't try to succeed perfectly, try to fail

So, this is not "bringing it to the 21st century." I feel like what would actually do that is related to the idea of don't try to succeed perfectly, try to fail elegantly? I want some sort of non-destructive way for "the shell" to take a best guess at what's going on when I make a typo, or when the data's not formatted quite right, like a live linter that's there all the time.