340/416 vs 383 vs 440

If he's gonna seriously step up his hp most everything gonna need to be upgraded probably anyways.

He could sell his 340 with headers rad bell housing etc... Go towards the trickflow topend kit.

440 with a trick flow top end will easily eclipse just about any small block build at similar cost. I dont see any advantage staying small block.
Thats because you ignored my post.
Ether way, it's his call.
For me, when I did my /6 - B block conversion, it was pricey. It would, cost the same as a small block from a /6. But he already has a small block there. IMO, the B/RB pays off well if your racing. Not so much otherwise. He will need a new trans, perhaps a new drive shaft, depends on the rear end thats in there now. If he makes a worthy big block, AKA, serious power, he will need a rear. Better radiator since a real powerful big block will not cool with a S/B rad.
How much for all the upgarded parts?