Opinions wanted: 408/416 Stroker or 440?

If it's in a B body - I'd say go big block. A stroker small block kicks ***, but a stroker big block kicks bigger asses further. MOney-wise the big block will be about 25% more cash for a like build. So for you, having a block helps the small block side. You'll have to buy a big block, a bell and flywheel and clutch, and headers or manifolds. So the big block will end up being a bunch more.
BUT - a small block, any small block in a B body will not get much for respect. Even if it's fast.
Strokers of any size need the best heads you can afford, and a camshaft bigger than the cam catalogs list for a street engine. (very basic there...lol)