What pushed me toward Timbuk2 was the number of pockets and compartments inside -- its bags aren't just buckets with a strap. Moreover, in addition to getting a bag that looked exactly how I wanted, by going custom I was also giving a job to one of Timbuk2's San Francisco bag-makers, and I'm all about supporting domestic manufacturing whenever possible.
I wasn't sure a medium would be big enough after scoping its dimensions online, but when my bag arrived just over a week later, I was happily proven wrong. My current haul is a five-subject notebook, a 2-inch three-ring binder, hardcover versions of Jurassic Park and Blood Meridian, a Moleskine, my 13-inch MacBook Air and PS Vita. That's not the half of it, though, because I'm also schlepping all kinds of wall adapters and charging cables, a smattering of writing instruments, business cards, two voice recorders, a few paperback novels, two notepads and a travel mug. Heavy? A bit. Disorganized? No way.
I'm horribly scatterbrained, but I have absolutely zero problems finding anything at a moment's notice in this bag. The pouch inside a pocket that resides inside yet another compartment isn't just a feature that'd make Xzibit smile; it's something I use constantly. The pack has a safe and secure place for everything I'd want to carry with me and more compartments than I'll probably ever take advantage of. For me, that's priceless.