Small block to big block?

Go big. You may or may not need a new radiator as both big and small blocks have the option of WP inlet on either side. BUT, the radiator may not be up to cooling your new engine. We have a factory 340 car and have built a couple of 440 cars. I don't build anything with huge cams, etc. The difference between the 340 and 440 is tremendous. There's just really no comparison on the street even if there isn't a huge difference in quarter mile times. As for fuel mileage, not much difference there, either.
Awesome that’s the kind of real world info I appreciate. I really wouldn’t have questioned it much until I drove my dad’s big block Chevy car. It’s a massive heavy car but it felt so much better down Low in the rpm even though if we raced I’m not sure that he would actually go faster over a 1/4 mile. It was a fairly mild build about 525 hp and similar torque.