With a supercharger you can have the best of both, mild cam for cruising and the power for when you need it!

If you want to build for 550hp/torq, go with a set of edelbrock rpm or 440source heads and a piston with a compression height of 2.060 or taller. That way with some milling you can get an honest 10.5 compression which with that cam and pump gas will do what you want. Then a set of headers and a good intake like a holley street dominator or edelbrock rpm. Carb you'll want to step up to an 850 since you'll be revving it over 6000rpm.

I say build the high-po street machine you want. Just stick with a carb that has a choke(tune the carb well, including the choke), recurve your distributor to setup your advance properly and run the right stall converter/gearing for your cam. That will help it be as driveable as possible.