I went up to the 257 to carry a macbook pro 15" and your other ideal load components. The 256 could fit them--barely, but was so tight it made it impractical for everyday use for me. Also, the big toothed zipper on these tends to scratch your hands and your computer trying to get things in, particularly when filled to capacity. I found the bigger back works much better when trying to haul a computer as well. I think these bags work best for what they were originally designed: papers, books, pens and other small items, not computers. Also, the 257 in real life does not seem as wide or bulky as the measurements suggest. Perhaps because the soft sided canvas droops a little and pulls down under load, making it seem less wide. The 256 is still much sleeker though (if you can call any Filson bag sleek).
