I'm not sure if my KS Mountain qualifies as old school. It's only 30 years old but if it helps I'll just shoot old school bullets from it. For a shotgun the pragmatic side of me says my 870 12 gauge. I shoot it well and it will handle anything. The romantic in me says my Cogswell and Harrison 12 would get the nod.
As for the third, I'll cheat and take a lefty Charles Daly 222 with a chamber insert for 22 LR.