ANYONE HAVE ANY IDEA HOW FAR YOU CAN STROKE A 360 OUT TO?

Hey guys, I'm trying to decide what I'm gonna do with my challenger engine wise, it has the matching numbers 318 in it but its just simply too weak. A car like that needs to run and drive as bad A$$ as she looks lol. I'm trying to decide to either build the crap out of the 318 that is in it or get a 360 and stroke it out. I know the 360 stroked out would get me a ton more torque and ponies. So I'm kind of leading towards doing that cause even though my 318 matches the car it really doesnt help the value of it, infact it would probably increase the value if I put something worth talking about in it. And I would put probably put about the same amount into the 318 build as I would the 360 and come out with ALOT less power. I know you can go up to a 4 inch stroke on the 360 which gives you a 408 stroker. Can you go any further than that? And even if you couldn't go any further than that will any special modifications have to be made for a 4 inch stroke crank?

Also I'm going to hunt down a 4 speed for it or 5 speed if I can find something that will work(any suggestions on the 5 speed are welcomed also), and I want to put a pretty hefty Cam in it, do you have to have a racing clutch in it to support a motor with around 450 to 550 HP and Torque, with a big cam? Or is it just a matter of maintaining RPM enough to keep the motor running to take off? It will remain a street car, and I plan on keeping compression around 10:1 maybe 10.5:1 to run on pump gas.