If I was given a nice stash of cash I wouldn't invest a dime into a new Mopar head. I might possibly be willing to fund the development of a cast iron block though. I know roughly what I'd do. It would be a low deck, 4.500 bore, stock replacement type block but with cross bolted 440 size mains. Probably some tweaks on the oiling system but that would be about it. I'd wave some money at Dart to see if they would handle the casting and machine work since their stuff tends to be really nice. I'd probably lose my shirt on the deal but if it was lottery money I wouldn't care too much.
I see no reason for a new head. TF240 is the perfect street head, Indy 440-1 is a great race head. NA guys who want to make more power are few and far between.

I do think I'd need to spend some money to also tool up a really good low deck intake since the market is a bit thin in that area, and I might go ahead and cast a really good set of valve covers since nobody has managed to do that.