Which will get to the end of 1/4 the quickest

Power to weight ratio the 440 would definitely run quicker. There is no replacement for displacement !

I have to agree my brother has a 3350lb aspen R/T with a .060 440 stoke stroke ross psitons 12.5 to 1 906 heads big valves ported with the 312 .590 cam. It has a 4400 stall and 4.10 gears and in bad weather goes 11 teens at 120 through exhaust and in good weather 10.80 at 122mph. No way a similarly prepared stock stroke 340 could do that twisting only 6000 rpm. Okay no rip me apart! LOL