I carry this one most days. Not too heavy and is a bit stylish while not out of place in a business situation. Very comfortable shoulder strap. My main complaint is the noise it makes when the metal pieces rub together on the strap and strap mounts.
I usually have iPad, Camera, Pico Amp/DACs, Overdrive wifi thingee, Pen, Pencil, keys, crappy Dell laptop, JH13 case and have no problem carrying all.
They make a smaller one but I am not sure your files would fit in the smaller bag.
Most days I would prefer a Messenger bag and as my Jack Spade is officially worn out I am trying out new messengers. So far the Cole Haan is my favorite.
Both bags have newspaper bag sizes that I will probably pick up at some point for the days I only need to carry the iPad.