360 or 340 ??????

So a 340 stroked to 416 is the way to go.

Umm.....no....
360, no need to stroke it, play to the 360's strenth. A good aluminum head with a 4500-5500rpm torquey cam with an intake in the same neighborhood. Its really all youd need for a boulevard bruiser.

Sell the 340 to the guys willing to pay big bucks just to turn around and spend more big bucks stroking.