I already have a custom Timbuk2 Classic Messenger (Small), and considered getting one of the newer XS ones. Overall, I like the Timbuk2 bag, but my main complaints are that the strap length is too short, and the shoulder pad moves too much (find myself adjusting it constantly). I decided to get something else.
I ended up going for the Tom Bihn Ristretto for iPad (Black/Steel). The bag was smaller than I imagined, but it has a good amount of compartments and looks like its going to carry everything I need.
I've been using this bag for about two weeks now and I really like it. It's a smaller bag, so it probably can't compete with the Timbuk2 Classic Messenger in volume, but it holds it's fair share.
The bag is handmade and the quality shows. The material used is excellent and very sturdy. The bag was sent in a UPS box and is not sealed in any type of bag. I mention this because a very minor complaint I had was that the bag was a tad bit dirty since the box isn't air tight and dust/dirt from the truck found it's way in.
The back has a compartment for a magazine or similarly shaped item. There is also a small nylon like handle, but is placed where it does not stick out over the top of the bag. The bag also comes with an adjustable waist strap, but I have removed it.
All the parts used appear to be top notch. Part of me is going to miss the velcro sound of the Timbuk2, but snap is an acceptable replacement.
The accessories compartments:
The first open pouch right above the clasp is about 7" deep at it's shallowest point and 8.5" wide.
Right above that are 2 pencil/pen holders, and 2 phone size holders (5" deep by 3" wide).
Right above that is a little ring you can attach a key tether to. Then above that is the zipper pouch (also about 7" deep and 8.5" wide).
The next compartment is large enough for a notebook, magazine, etc. It's about 11" deep and about 9+" wide. The back is padded (behind it is the iPad/Netbook compartment) and could be used for a keyboard or other similar type accessory. There is also another ring in this compartment along with a removable key tether. The rings in this compartment and the other are identical so you can place the key tether on either one.
The iPad/Netbook compartment is padded on the front and back. It also has a padded flap that tucks in. The front inside of the compartment consists of a very soft material, but the back inside is made of the same Cordura material used on the exterior of the bag. I initially thought this was an odd choice, but Tom Bihn assures me that the Cordura fabric may be touch and sturdy, but is soft and shouldn't cause any scratches. This is a non issue for me since my iPad will be in the Apple Case, but anyone considering this bag with a nude iPad may want to put the screen towards the softer side.
This is just an example of what I am carrying in my bag right now, or at least the past couple weeks. It's a good amount of stuff, and there is still plenty of room for more.
The pocket in the interior section is perfect for the Overdrive and/or cables.
Here's a shot of the iPad in the Apple case in the padded compartment.
If I were to list any negatives of this bag I guess one would be the back sleeve/pocket (seen on 2nd image of my first post). The Tom Bihn site states this is, " ideal for storing papers, a magazine or a newspaper." I don't think it's quite deep enough for an average size magazine. I tried my issue of Maxim in there and it stuck out too much and interfered with the handle. I think it will still be useful for smaller documents, but not average size or large magazine/documents.
Another negative, and this is kind of nit picking, is lack of color options or custom colors. This is one of the things I love about Timbuk2. Even their stock color options are plentiful, if sometimes a bit odd. If you don't like the stock options you can always custom order from a large variety of colors and patterns. At this time, Tom Bihn only has 4 color options (Black/Wasabi, Black/Steel, Cocoa/Olive, and Olive/Cayenne) and all sold out :p.
The only other negative that I have noticed, and this is completely IMO, is the back side of the iPad compartment. As I mentioned in my first post, the back side is made of the same Cordura material as the exterior of the bag. It is still padded on both sides, but the back side is not the same soft material as the inner side. I don't think this will scratch a naked iPad, but I found it a bit odd and worth mentioning.
This bag is sized right to carry the iPad and other essentials, but is not large or bulky. I came from a Timbuk2 Classic Messenger and feel this is a better option for taller (6' plus) people. The strap is plenty long and the shoulder pad does not move around too easily, which were my main complaints with the Timbuk2 bag. The bag is just comfortable to wear, and looks great (IMO) while protecting your iPad. This also being my first Tom Bihn bag, I was not dissapointed! This bag has the superb quality that I have been reading about. This is a great bag for new iPad owners.