Does the bag have a strap on the back to slide/secure it over a standard roller luggage handle? As a business traveler... this is a must have feature.

There is a version of this bag from Samsonite sold elsewhere that has the luggage handle strap, but it is way more expensive. Up to you...

Does this bag expand well or is it rigid? (i.e. If i stuff a bunch of thick books and files in here, will it accommodate?)

The bag is really flexible but the space inside is not huge as there are cushions for the laptop. Personally, given I use it at work where I do not carry books but a few papers is pretty good and I am more than happy. It really depends how many books you want to carry. I would say, comfortably it can accommodate 3 200 pages A4 soft cover books plus files but still it is something I haven't tried.

Do you have undo the buckles on the outside flap in order to access the inside or can those metal devices under the buckles be released?

The buckles are for decoration. There are easy metal snaps under the buckles. This bag has a very professional look and plenty of Zippers and pockets inside. Quality is much better than I expected

Does the strap have any padding on it for shoulder comfort? (Like: http://www.amazon.com/Kenneth-Cole-Reaction-Luggage-Bus)

Yes it does have a pad for your shoulder, and its adjustable too. It's a lot like the pads on a Rebel, or Canon camera carrying bag. Also the pad has nice gripping texture on one side, which reduces any extra sliding around when you're wearing it while walking. No worries though, the texture isn't like Velcro so it wont grab your clothing.

Samsonite Colombian Leather Flap-over Messenger Bag, Brown, One Size, Braun

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