340 or 408?

Depends how you look at it, from a drag racing point of view your only concerned about stall to shift points there's no reason a 340 can't make as much and or more between those two points just gonna happen generally at higher rpms.

Yes the larger the engine is almost always gonna make more low end power, but smaller engines are generally gonna/should run more gear so at any given mph they are gonna be running at a higher rpm possibly making the similar hp.

Here's a 302 vs 327 vs 350 the 302 and 327 built identical the 350 has a different cam.

Now down low the power band are fairly spread out but with the right gearing eg.. The 327 makes the same power as the 350 but only around 200 rpms more at lower rpms so just with a little bit more gear the 327 match bottom end power plus got all those extra top end rpms. Which is more streetable ? probably the 350 and the main advantage for most it needs less gearing. Now the 302 needs 500-700 rpms down low which you ain't gonna get without crazy gearing but with more gearing it's going be closer in reality then on this graph.

Yes if you just run the standard 3.55 gears the 350 probably be best all around which to me is the main benefit of displacement not needing as much gears.

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Trust me I definitely understand the general sentiment. But if you're looking at what you would actually feel by the butt dyno, The larger displacement area under the curve difference is huge.

In fact I would go so far as to say that even properly geared stalled etc the bigger engine is going to win by virtue of that increased area under the curve. It's making more power across a broader RPM range you can work with that.