440 w/weiand roots style supercharger

Take it from me, you won't scare the import kids because they're too ignorant to realize what you have. They rev their little 4 cylinder weed whacker engines at me like they're just as bad!
Anyway, like already mentioned, get a custom cam designed for blower use. Also, spend the money and get a pair of carbs designed for YOUR blown engine. I've been down that road of trying to make stock carbs work. I finally spent the coin and got a pair of custom built blower carbs from Quick fuel Technology. Big difference in power and driveability.
Get big tube headers and build the largest diameter exhaust system you can fit under the car.
Don't waste your money rebuilding old factory iron heads, buy a pair of aluminum heads. Indy EZ heads would be a great choice.
Now, I can tell you right off the bat, you're going to have some clearance issues to deal with between the blower belt and your radiator, specifically, you won't have room for an engine driven cooling fan. The easiest solution is to mount a pair of HIGH OUTPUT electric fans in front of the radiator. Not the best solution, tho, because you lose about 20% efficiency when you mount fans in front of the radiator instead of behind it. You'll have to mock everything up and decide what course of action you want to take. You can see on my website what my solution to that problem is.