355 or 383
The 383 has more TQ than the 355 and if you don't have the tires & suspension set up for the added n2o, then the old saying of "Spinning isn't winning!" comes into play. I would pick the motor combo to match the components that you plan on useing in your car's chassis.
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a 355 and a 383 are going to cost the same amount of cash in forged parts. the only thing i would do different besides the crank (duh) is i would run 5.85" rods in the 383 instead of 6" so you can have a bit more room for rings. most people go with a 355 because its tough to feed a high rpm 383 properly with a stock head casting. but when you're on the nitrous i'd say you wont have a problem getting the power you should from a 383. nitrous will cover up alot of sin in the top end.
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The bottom end, does not create horsepower. Just how 383astro stated, the 383 creates more torque than a 355. Either way you chose, getting a quality built motor is key. You really can't go wrong with either one. Personally I did mine a 383 because of the bigger cubes and displacement. The famous quote goes, "There's no replacement for displacement."