It's better to not cart every last piece of gear you own around. I'm fairly bad about dragging most of my gear with me if I'm driving somewhere, but if you aren't careful, this can really get into your way. Like my friend who was complaining that he dragged a bunch of camera gear around but didn't take a single shot.
I think it boils down to the minimum amount of gear you can do with finesse anything you might randomly want to photograph. Constrained by the size of your container.
This means that I go out a LOT lately with just my Canon G7, because it's so small and can fit within my bike trunk bag. This also means that I tend to bring either my 35mm camera or my Mamiya RB67 but not necessarily both. Likewise, I love my Sunpak 622s, but I've been carrying my Vivitar 285HV instead because the 622 is too big.
The interesting thing I've discovered is how well Hugin works. I can take a stitched panorama with no gear but the camera and my hands. I'll get a fairly high-resolution image out of it and, as long as I'm careful, it'll look quite seamless.
I think that organization plays a role. See, I've always got a backup for my memory card on my camera because I stuffed a Micro SD to SD adapter in the digital camera's little velcro compartment and I've got a Micro SD card in my phone. If I can grab a single case for some batch of gear, it works out better than individually picking the pieces I want to bring today. Because the FlashZebra adapters are so tiny, I tend to just leave them mounted to gear when I put it away.
Upon realizing this, I decided to start work on this problem more carefully. I think it's an optimization problem. For my bike, I've got two sets of bike bags.. one small trunk bag for weekend adventures that sits atop my rack, and one pair of panniers that hook to the side of the rack for actually hauling stuff. Some things I'd rather not have to buy multiple copies of, so it works out better if I can move some of my roadside repair gear between the trunk bag and the panniers. And it also works nicely to be able to empty the panniers if I want to carry groceries in them instead of my laptop and lunch. So I worked out what was actually important to have at the same time as I'd need something else, what needed to move between bags, and how to package things up such that my bike bags are neatly organized.
I think the same techniques apply to the camera bag. I'll probably write some more down the road, once I see what works.