I own a 257 and the saddlebag briefcase. The saddlebag is now my everyday briefcase. The design is much more suited to today's technology advanced business person. As far as organization is concerned it's a well thought out bag. Laptop sits in it's own compartment. The other compartment has dividers in it to keep things organized. Its possible you could use this compartment for a change
of clothes or two. It's got avmagazine compartment on the back and the two flapped pockets hold all the small stuff and keeps it organized as well.
Mine's loaded up and weighs over twenty pounds. The shoulder strap does come in handy and is relatively comfortable. I would not run with it though. Sounds like it would be a bad deal.
With all of this said keep in mind the 257 is still a great bag. I switched because I carry entirely too much gadgetry and paperwork for my own good.