When cutting the pin, the overcutting is usually minimal, just enough to release the fibers in the corner. You mostly see these very long overcuts in the socket, where there is plenty of wood around to keep up the integrity of the piece.
Those guys may have been "sloppy", they sure weren't stupid.
And I don't think we can draw any conclusion from the fact that the majority of antique furniture didn't survive. The most important factor was changing fashion.