Opinions wanted: 408/416 Stroker or 440?

From the weight perspective, there's only about 150 pounds difference stock for stock.
That's right and once you aluminize everything you can on the big block engine, the weight difference is gone. The car will act like it has a small block in it weight wise.

Edit... I didn't realize the car was a B body. I'd big block it, but as I said earlier, your car, your way.