Being a past girlie owner of a 2001 1200 XL (which really wasn't so girlie as folks have pointed out), I "saw the light" after my demo ride on the America. If he's looking for a comfortable ride, the SM/AM will have his vote in 2 shakes...folks have discussed the higher center of gravity on the Sporty, and for me I got tired of getting off a bike feeling like I'd been on a jackhammer for 6 hours, despite the nimble ride and excellent cornering. Not fun on long rides, frequent fuel stops which my numb hands needed to get their feeling back. The other differences were already mentioned.
I had 3 other HDs before the 2001- an 84 Sporty, a 92 Lowrider, a 79 shovelhead. Beautiful bikes all of them (my favorite was the shovel), but my Pretty Bonnie outshines them all. Comfort, handling, performance, heritage and style.