Size Matters
Less is more in this business.
It's a hassle, particularly if you commute, to cart a bunch of stuff around. That having been said, I do like to carry my laptop with me on trips. I've tried a couple of different remedies.
First, I bought an "office" roller, made by Atlantic, that has a special, reinforced section to carry your laptop. The case is about 2/3 the size of your typical airline rollboard but I still manage to enough for a four-day trip inside. The laptop slips in-and-out of a size, zippered compartment, allowing easy access at security. The case works great. The only downside is that, because of it's smaller size, my flight bag drags a little on the ground when it's attached to the luggage. I have to hold the luggage a little lower then I normally would when I walk to avoid the drag. I'm still working on a remedy for that.
My second remedy is to carry the laptop in a separate, reinforced attache case by Pelican. It's a model 1470 with "pluck-and-pull" foam that you customize to perfectly fit your laptop and accessories. It works great and is literally indestructible. I sit it on top of my Travel Pro (with the flight bag attached to the back) and it works pretty well.
I hope that helps. Good luck.