Just in case there are folks debating buying an Arkel Bug and watching this thread, I wanted to give an update on my situation.
I just got off the phone with Yves at Arkel and he was very helpful. He recommended that I switch to an Arkel Utility Basket, which has more room inside and less specialized pockets and things that take up space. I also discussed my heel clearence, my stay length, etc with him, and he recommended an OMM Red Rock rack to ensure I can use the 1 big bag and not have heel clearance issues.
I will say, the Bug was an excellent product. It looks nice, it has all kinds of great ideas in its design, and I think people who aren't looking to carry so many things in 1 bag will be extremely happy with it.
I definitely recommend calling and talking to the folks at Arkel before buying. They did take a few days to get back to me, but once I had their attention, they were extremely helpful.
I'll post a review of the whole setup once I have it in place.