I have a set of 30 over Icon Forged pistons I could sell you for your 408 build. only used about 1000 miles if that. Long story as to why they barely got used, happy to discuss in PM if you are interested....but they are perfectly usable.
my 408 (now a 410) makes 592hp/577trq. ran a 12.2 with an open diff on street tires slipping off the line in a 3200lb Dart.
Over the years I've had both, a few times. Me, I really like the stroker over the 440. The front weight, and the quick response of the stroker make it slightly more favorable for me. For the street I would go with a stroker, especially with a 4-speed. More cash than the 440 for sure, but if that isn't a deal breaker stroke it.