First of all, thanks to everyone for their help. This is an amazing community.
With all the input, I'm now considering these two directions:
Tristar with Brain Cell
Pros: slightly cheaper than option below
Cons: have to completely remove laptop at checkpoints, tight fit for cables
Tristar with Cadet
Pros: Cache on Rails, ample storage for cables
Cons: Expensive, possible tight squeeze with Retina MBP in middle Tristar pocket
I'm leaning towards getting the Cadet even though I wasn't looking to part with that much money. That said, I don't want to regret spending a little less and not getting a good system in place.
Feel free to chime in if anything here looks crazy.