Good that you are asking yourself this question...The typical first response when someone wants to customize their car is, "What do you want your car to be", except this is obviously a cruising car, not a dragster.
Cruiser sounds like what you want... and start thinking about what you expect in a cruiser.
You can't beat a stroked 440 for a heavy car. You want low end torque to move the weight.if I am looking for more oomf, torque, horsepower out of my car, is it worth switching to the 440 or should I stroke out my 383?
It's good until you mention the blower. Now you are adding $$$ and lots of complications to the project. This sounds like it's a first build for you, so I'm going to suggest you stay with a more conventional build. A stroked 440, the right cam, rear etc. (think package) can be a ball to drive and fast enough to scare yourself from time to time. With a supercharger, you are looking at custom forged pistons, racing gas, lots of tuning to get it right and on and on.... Read that as a lot of time and money..... and along with that the fun just starts draining out of it...I know it sounds crazy and stupid, but I have this custom vision of my black beauty with a 440 in it, B&M/TCI tranny, updated rear gear and a supercharger.