340/416 vs 383 vs 440

I would look at the pros and cons... Wouldn't take much to get 500 horse out of the 440. 340/stroker will get there, but probably be a more radical build. At the power level you are wanting, both would easily get it done. So it comes down to working on it in the car, yeah a big block sucks. But I would think that the big block will last a lot longer, with the stress on the main caps, and block stress. Jmo over or at 500, I would go BB.