I can only speak about the Office bag. I have had one for nearly 3 years and during that time used it about 4 days a week, year round.
The quality is outstanding. While looking a little worn, I estimate the bag to last another 2 years before I need a replacement.
The inside is one big partition and cannot really be extended. Carry too little, and it might bounce around, carry too much and you might have trouble closing the roll-top. I would guesstimate that your stuff would fit in the Office bag nicely, although a full-size laptop (I occasionally carry one in a sleeve) will easily fill up half the capacity
Whatever bag you choose, do yourself a favor and order from TheTouringStore.com. Competitive pricing, free shipping and the best service in the industry