340/416 vs 383 vs 440

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?

Actually, all he'd need is a bell housing. If its a true 340 4 spd, it should have the 8.75, which will handle a 440 powered street tire car just fine. Only thing different he'd need is engine mounts and maybe a radiator, which would likely need upgraded for longevity with a 500 hp built 416 anyway, same with the belhousing, clutch and flywheel. Dollar for Dollar, not much cost difference in building a 416 or a 440. If anything, I'd argue that a 500 hp 440 would be cheaper to build than a maxed out 416. However, for the same money as the 416, he could build a 600+ hp 440.

The biggest thing to me is this, the weight. If he does runs aluminum heads, intakes and headers, water pump etc, he can get that 440 weight down to that of a small block's stock weight. However, on the same notion, those same components shave the stock 360 weight down even more.

All that said, and having both a 408 stroker in one ride and a 440 in the other and having built and driven a 451 equipped charger, assuming I was going to be dropping the same coin for either option, I would actually opt for the 416. Reason being, it is a true H Code 4 speed car and one day, he may want to reverse course and go back to the original setup. Easier to do that, especially given some of the other mods to clear things in a RB A body that are much harder to return to original (Blower motor deletes, fender mods, etc)