440 compression boost

Not sure on heads yet. i'd like to either go closed chamber 915 or aluminum heads. it's gonna be a street/strip car

You have to pick the heads before you pick the pistons, or you have know the chamber CC.

If you are going to spend money on a set of heads there really isn't any reason to use cast iron heads. It's not very hard to approach the cost of an entry level aluminum head when rebuilding a stock head.