Brainstormin' 440 vs 5.9 ...
For myself, it will ALWAYS be small block. No matter what chassis, ALWAYS small block.
That said, you have been talking about the 440 for a while. Why not put the 906 and 452 heads for sale on marketplace, then whatever set sells first, keep the other set. Then add the money to the $500 budget.
Have you had the heads off of the 440? I wonder what the cylinders look like.