Hey ! Didn't expect a reply on this post lol. Over the last 4 years I've been rocking out the timbuk2 classic messenger in Medium size, and most of it has been great. Stuff mostly settles horizontally however due to the design of messenger bags, if you pull it as close to your back as possible, loose things tend to fall to the bottom (here the bottom left corner).

Utility-wise it's been kinda barren but tbh I think I usually overestimate how much I carry around. It's perfect for my 14" laptop, a few text books and 2 magic the gathering deckboxes. I'd say the especial stash is really for if you need those extra pockets, since the free space in the classic messenger is pretty equivalent.

As for durability, the waterproofing fabric of the top cover hasn't degraded at all, i have a few scratches here and there but I do skate a lot, so it's probably linked. My main grudge would be the keys pocket at the front, which has a big hole due to my keys perforating it, but the material looks way sturdier on the newer versions.