340/416 vs 383 vs 440

Why spend $3000-5000 on a 416 short block to come up with an engine that 30 cid smaller than a stock 440?
Because it is cheaper and easier. No more, no less.
He retains the same trans, driveshaft, cooling etc... and other small parts that go with an engine swap. This saves a lot of money which can be rolled into a set of heads. Fully ported Edelbrocks, or Victors, or wait for Trick Flows?
The added weight of the B/RB can be a minor offset as well.