I own a 2003S Box and by far is the sweetest driving machine I've ever had. Your query is very astute and reasonable. Similarities in body styling is a given and are looks are pretty much the same. The features that would sway me to the 2003S are the : the brakes, and the engine. In the S you get the brakes of the 911 which are fantastic and the engine is more powerful developing 260 hp. Being in the forum here has illustrated to me the cost of each hp you add to the car and it always seems to be outrageous. Therefore get the more powerful engine with the much better brakes.
Of course this goes without saying all things being equal. Cars of comparable wear and tear and similar condition. In any event good luck in your quest and welcome to our Group in the future.