The only part that I think could be a little less padded might be the 'front' section of the bag (where the outer zipped pocket is). Now I do have a mini tripod and a rocket blower in that front pocket, so it might appear to be a bit more 'bloated' in that area than it actually is (actually just measured the padding, and both sides and the front are 1" outside measurement each). So whether that much padding on three of the sides is 'too much' or not depends on how much you feel comfortable with. I mean, I have a Domke F803 and the big complaint about that one is that it has too little padding.
And as far as anything falling out of the sides, I really can't see that happening. The flap closes down pretty snug, and even if you left the flap unclipped it would still be fine (I road-tested it this past weekend and it seemed fine to me). Just to test it out now, with the flap clipped shut I took the bag and turned it sideways and shook it, and nothing came out. The only way something would come out would be if you turned the bag completely upside-down and shook it. Plus, there's the nice wide strap that would also prevent anything from falling out of the sides (assuming you have the bag hanging from your shoulder). As far as someone slipping their hand in the side and pulling something out, well I'm going to NYC soon so we'll find out!
A word about water resistence -- the outer canvas is a waxed cotton, so it should hold up fine. The big red flap is obviously leather, so if you were really concerned about protecting it, you could add a coat of Dubbin to it. The tapestry pattern, can't say, but it's canvas-backed, so I think it's fine.
Repair-wise, I think if there were ever an issue, I'd just send it back to Robyn. Now having said that, I did have my upholstery friend do that 'fix' to the interior dividers. And actually, that may be something else that some photographers may or may not like, which is the fact that the dividers are sewn-in, rather than velcroed. I can really go either way with that, so no biggie for me. But the bag seems so well made that I can't see anything that would require future repairing (they don't skimp on the 'quality' in Grand Rapids!). My upholsterer friend even commented on how well-made it was, and he knows a thing or two about fabric and construction.
Pulling the camera and lenses in and out of the bag is not an issue at all -- nothing gets snagged, in and out easily, nothing gets lost. Here again, the only thing that I found out right away was that the dividers were too long for my Leica lenses (and I have two mounted back-to-back on each side, so 4 lenses total plus the Noctilux on the body), but my upholsterer friend did the quick fix, so now that's not an issue.
Overall I think it's a good size -- I don't think I'd want anything smaller, and the bigger one is too big for my specific need (Robyn told me that one would hold up to 50 lbs of gear). So all in all, I'm happy.