I've got to attest to the quality of the extra small Timbuk2 Messenger Bag. I ordered a "build your own build bag" custom (2010 revised) Messenger Bag Tuesday night last week, it was shipped last Wednesday, and I received it today through UPS Ground. Wow. This is what I've wanted and more. It's just fantastic. It was shipped in just a plastic UPS bag with no padding whatsoever from their San Francisco warehouse to me in New Jersey. I guess that's their way of saying "hey, our bags can travel the entire country without any real padding and still arrive looking brand new".
The bag has more room than I was expecting, which has got me thinking about what I can add to it. For anybody who wants to carry around an Apple Wireless Keyboard with their iPad like I do, there is more than enough room for that in the main section of the main compartment. There are a lot more compartments than I was expecting. I was just thinking of carrying around my iPad, an Apple Wireless Keyboard, and some cables. Well, I can easily throw in my incredibly underused camera and its charger and extra battery. My first generation PSP (though I don't use it at all, and it really does show it's age) could fit, but I won't add it. My Apple headphones will go in there as well. So could an iPhone battery pack/battery case. As well as some movies/games in their standard casing.
And, check this out: There's enough pockets for everything listed above to fit in a seperate pocket, and you'll still have extra pockets. So, my custom bag was handmade and shipped within a day, the quality is fantastic, the bag looks great, there's more than enough compartments and pockets for pretty much anything you could carry, certainly enough pockets for more than an iPad and a few extras, plus the bag is still small. My only complaint is that there could be some padding on the bottom and throughout the rest of the bag, though there's a hint of padding in the front and the sides.
Around $145 for the bag plus a good strap pad shipped was a decent price. I did buy a $125 gift card for $95, so I paid $30 less than what it normallly is. The pre-made bags can easily be found for around half the price, but I liked Timbuk2's emphasis on cool-looking bags, but I didn't want any crazy color combinations or anything too boring, so making a custom bag that was black with "gun metal" in the center and a red logo fit me well. Timbuk2 seems to make the best iPad-sized bag on the market, with enough for all of your iPad essentials, and you'll be surprised at how much more will fit. I'll post a revised review with pictures next week of this 2010 extra small Timbuk2 Messenger Bag.