I'm biased...I have the glazed espresso and love it. It gets smooshier the more I use it. The chocolate is too matte for me. The glazed espresso's on sale at lunaboston for $500, plus 20% off with "grechen".
I have the Glazed Espresso MA and love it, but in the Matinee I prefer the chocolate for two reasons - (1) the glazed espresso looks great all by itself w/o the "distraction" of the suede flaps and (2) I think the Matinee is better w/a little thicker, softer & smooshier leather. The chocolate bag looks smooshier than the glazed espresso (altho the leather on the glazed espresso MA is very soft & thin). With the softer leather, it makes the bag easier to carry, especially on your shoulder (because the top smushes down). I have the Matinee in black/blue and the leather is very thick, soft & mushy - I can easily fit the Matinee on my shoulder but not my MA.
I love my Glazed Espresso MA but I don't think I'd like it as much on the Matinee.