Thanks for playing! and for the patience, as it's taken me a while to get back to you. :)
I really appreciate the thoughtful message. In that first example, I chose to be extra permissive to avoid annoying the player. It doesn't enable unintended solutions or cause any issues, so I decided to allow it. Ideally it would be accounted for in the animation (the player pulls the crate towards them as they turn) but I never got around to implementing that.
The second example is fundamentally disallowed by the system. It would break most of the game to allow it.
While i agree that it's very easy to argue that the first situation has too much clipping to be allowed, there's still a pretty big difference in the two scenarios, as you can see here - 
So at some point I have to draw the line of "that's too much clipping", and I chose "when a face of a crate/block is pushing directly against the face of another". Hope that's a satisfying answer!