Opinions on 360 vs 440

You have a fresh 440, and a tired 360.
If you just had the 360, and needed a 440, the answer is simple, build the 360.
But I suspect you WANT the 440, or you wouldn't have bought it and freshened it.
Put the 440 in it.

If I had a 360 that I could stroke to 408, that's what I would put in my Barracuda (67 notch). Since the only small block I have is a 273 2bbl, and I have a 511 laying around, it's gonna get a big block.