The Pros are a nice idea with the padding and comfort - but they never fit as well as the classics.
The classic's don't last though - the pros are better at durability, but the sizing/fit doesn't compare. It's as if you can't have the concept of padding come into the classics, otherwise you lose something in the process - this is more or less what I have found.
I just got these Old Skool syndicates, but they're a little large for my normal 10.5 size (but I've had half cab pros in a 10, and it's too small where my toes hit the front, had to return them - having a fat foot for skate shoes is such a hassle...) - love how they skate, but they aren't as good a fit as the originals. Vans know this and loves it - their shoes normally last like 2 to 3 months if you skate them a decent amount. Just means you gotta buy more vans...