440 vs 360 barracuda

First off, sorry if this is in the wrong section. I have purchased a 4006630-440-8 stock 440 engine. I am seriously debating on putting this engine in my barracuda with TTI headers. It has manual brakes and steering so I'm not worried about losing those. To make it worth it to me, I would want 500 to 550 horsepower and a lot of torque. I would want to build it with weekend street-ability in mind. I'm talking 10:1 compression at most, .550 lift cam 110-112 degree separation with aluminum heads and dual plane intake. My question is (assuming this power level is do-able with the compression and cam): how street-able is a ~525 horsepower 440 when considering daily reliability, fun, and cooling. I currently have a 380 horsepower 360 magnum with a 4 speed (3.55 rear gear) and cal-tracs. It has a single plane intake (650 carb w/ mech secondaries) but manifolds not headers. I absolutely love driving this car as a daily on weekends, but I want to scare passengers a little more. I want to be able to do the same thing but with a big block. I can build the magnum up to around 450 horse with relative ease, so is it worth it to put the big block into the car? I do not want to take time, MPG, or money into account as these are not deciding factors for me. I fully understand that it would be much cheaper to keep the 360. Also I'm 23, so street-ability may mean something different to me, that I'm not as concerned about ride quality, noise, etc. Fun is my main concern. Thanks