Sounds like the 58 and the 1100 have about equal sentimental value. From your description of the two, my preference would be for the 58. It is not too common in a vent/skeet barrel. Since it was made prior to the advent of shot collars, it likely has a slightly tighter choke than today's skeet models and will throw more of a imp-to-modified pattern. Try it on paper and see.

At any rate, your skeet model 58 is a super dove and quail gun. I'd sure hang onto it. You can pick up an 1100 anywhere, anytime, and one that's in better shape than the one you currenty have.