Brainstormin' 440 vs 5.9 ...

I get why no to the pistons, probably a 15-30 or so hp gain, lot of work and $$ just for that plus even with a big cam and low cr gonna at least make as much torque as a decent 360 if not more.
I think what the comparison in my mind really is, is this. Will a low mileage RV 440 with 4bbl/mild cam beat a high, high mileage 360 mag with 4bbl/mild cam.
I get the "low compression", but I'm also looking at 80 more cubes and bigger valves. If it's a wash, then I don't want the extra weight and less room under the hood. Nor the WORK !!! LOL