On a recent trip, I followed my own advice, to a point. I put the 24, 300, and F in the bag, then gave the rest of the space over to a C220 with 65 and 105 mm lenses.
End result: nice pictures, but wondering why I didn't take up weight-lifting in college. If I could get a true wide-angle for the C220, I'd leave the F behind entirely. Anyone got a biogon 38mm in shutter lying around? (I know; the real answer is split the difference and get a Norita-66 to replace both of them.)