One of my brothers is a H-D guy, and is crazy about his bikes. It isn't really the styling or the injection, etc. imo. Most H-D guys simply like that original H-D look, and the VROD is different. That said, I don't know many H-D guys who don't like the VROD at least as much as the Sportster. Most dislike the tank on the Sportster, but otherwise like the bike. It looks different from others mostly due to that tiny tank and that can be switched out. You can't make the same kind of changes with the VROD. Most H-D's don't leak oil anymore.
A former brother-in-law has 2 H-D's, one is a 2006 Ultra Classic, the other a 1976 Hardtail, which he bought new in 1975. It has over 200,000 miles on the clock, according to him and he's ridden it all over the country and into Mexico. He's even ridden it from NE Ohio to the Sturgis bike week some 15 times now. That guy isn't a VROD fan, but says he'd ride one if not for the preferred models, simply because it's a H-D. My brother has a 1999 FLSTF and it's about maxed. He adores it, and not only got rid of his Honda 1100, but also purchased two more H-D's since then, a Sportster he sold right away, and a 1999 Heritage Classic(or is that special?). He's down in FL now for Daytona's Bike Week and took a friend with a 2002 Sportster. Unlike my former in-law, they trailered the bikes, which kept them out of bad weather.
Those guys are all between 40 and 60, btw, so age may not play the biggest role. I think it's all about "what I want" when it comes to bike choices. Personally, I like crotch-rockets about at much as cruisers, but prefer off-road capable bikes most. Hence, my S/N.