The transition is not the issue, its the walking effectively into the screen to enter the cartoon short itself that is the issue. In DHS is works because you're going from the "real world" into the "toon world" to be part of the short. At TT where you're already in the toon world that same exact transition of "entering the short" doesn't quite work.
Now will it be the end of the world if they keep the same gag, no. Like I said we can just call it the TT Inception gag.
Besides at one point I thought you were all against this same transition being used because of these same points. I had actually agreed with you, so don't start disagreeing now just because I'm agreeing with you.