Good point on the low vamp. That leads to the third horizontal crease up in the middle of the vamp that you often see on broken in Barrie chukkas. Mine has it and it presses on my foot in an uncomfortable way.
Wear whatever will make highschool chicks have sex with you, assuming you're straight. If not, figure out what guy kids like.
Dressing like people on SF while in highschool will make you a very odd duck.
That's really too bad. If the shoes are actually "MTO" I don't see what's the difference in swapping a C width last when the pattern already exists. It's not like the pattern changes based on the color of the leather.