I think that there was a bit of a competition between Montgomery and his US counterparts, and that might have driven Monty to make some bad decisions. Haste makes waste, and the “bridge too far” was a matter of pride taking over on Monty’s part. His desire to beat those “yanks” caused him to take unnecessary chances.
Monty was not a cavalryman, so pell mell pursuits like out of Normandy (or North Africa, for that matter) weren’t his way of fighting. That is why I think he stopped after capturing Antwerp. He wanted to regroup and slow down. He preferred limited battles, so a deep thrust was not what you would normally expect from Monty.