Brainstormin' 440 vs 5.9 ...

Could be.... and I'm certainly not interested in a step backwards!! LOL
In my mind it certainly is, at least without doing more work than it sounds like you’re willing to spend $$ on.
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
Nope it won’t. They don’t make power, and they don’t run passed like 4800 rpm. Too many cubic inches for the dismal head flow and compression. They do make good torque but that doesn’t equate to low ETs. And on top of that they add a bunch of weight over a small block.