Should I go Big block or Small block?

My 2 cents.
Since you only give a choice of 4 engines, my thoughts
are, you can skip 2 of them the 318 and 340 because all
things being equal the 360 will always do everything better.

Again all things being equal the 440 is no more expensive to
build than a 360 and even if it were, no more than a couple 100 bucks.

Installing it into said vehicle is were things start to get sideways.
If you've chosen the 440, you already know you have to tighten up
your game because if you can get it to hook your gonna break everything
from the flywheel back.