Erik, I would go stroker. When I had my 417 built I told the builder I wanted a fun street motor and something that was going to be reliable. Here is what he built me:

340 block (0.035 over)
Eagle 4" crank
reconditioned stock rods
custom forged venolia pistons
9.5:1 compression (very pump friendly)
stock 'X' heads with 2.02 valves. (heads were cleaned up and good valve job done)
Mopar Performance 484 cam (241int/241ext, .484int/.484ext 108lsa)
Edelbrock Airgap intake
Holley 770 vacuum Secondary Street Avenger Carb
FBO ignition system
FBO curved distributor

On a chassis dyno the car made 375 peak RWHP and 484 peak RWTQ. At the flywheel the peak numbers are 420HP and 537HP respectively.

If you go through my build you can see that it is quite conservative. If I were to swap the heads for some Edelbrocks and put another cam with higher lift I could squeeze a fair amount more HP out of it but for my purposes this engine is good enough for the street and fun to drive as well as reliable. It also has a nice mean idle sound to it.

Unless there is a huge cost difference go stroker.