Should I go Big block or Small block?

ALL OF THEM!!! lol jk

sell off some of what you have, get a 400 block and cut the 440 crank or get a stroker kit, more power than the 440 with better fit and in a lighter package, what's not to love? Or a 420hp 360 is a relatively easy thing to do and that's plenty of hp for some pretty dandy street car ET's IMO