Of course, the ideal situation would be to run a "substitute" 3-speed automatic like one of the TurboHydramatics (metric TH200/TH350/TH400) behind a 409, but if it's a '62, '63, or '64, would it be restricted to a Powerglide (2-speed) since none of the Chevys had 3-speed automatics until '65 (and, the Turboglide 3-speed automatic was discontinued after '61)?
It would be a shame to win the battle, only to lose the war... I don't know how well a dual-quad 409 with a long-duration cam, in a heavy car, would like a Powerglide.... Maybe one with a deep 1st gear.... and a loose (7"???) converter.
Might make a good GT/AA combination....