If I can't fit what I want to take into a mid-sized bag, I don't take it. Carry too much stuff around and 1) it's too much stuff, 2) throws the back outta whack, 3) makes me waste too much time fiddling with gear exchanges than taking photos. Now I'm not working on projects or anything like that, I'm little better than a hack anyway. I've done the bagful of gear when I was young, and it was a real eye-opener to bring the 50lb bag of gear in from the car and realize that I didn't want a single thing in it all evening, except for a change of film.
One of my most oft-used bags is a Dockers airline carry-on bag, got it for $30 at a local retailer. It'll fit a couple of bodies with lenses mounted, a spare lens, a Zeiss Ikonta, a Stylus Epic, Powershot, film, batteries, etc. Way more than I need for a walkaround, and I'm going to pare it down for the next trip out.
My Mamiya 645 kit resides in a pair of bags: a Billingham 225 holds a body/grip/finder/lens, a pair of spare lenses, an insert, and some film. For more involved work, a Billingham Hadley adds a pair of spare backs, a few more inserts, more film, and a third spare lens if I think it really necessary. Spreading that kit out across two bags makes it more flexible, both for grab-and-go shooting and for the longer more involved projects. It also isn't a strain on one shoulder like it would be if it were all in a Pelican. (I have to admit I never thought of the rolling bag idea.)