I'll throw in my 2 cents. I don't think that Harley has, or probably ever will reach my demographic. I started riding at age 11 on a Yamaha, and have owned Japanese bikes ever since. The Harley name just doesn't mean and much to me as other people. I've had a chance to ride a few and wasn't really that impressed. I know that the reason people like them goes deeper than the bike itself, kinda like a brotherhood or fraternity.
I noticed this after talking to my Dad. After my Mom died he decided to get a motorcycle to pass the time and partly because he had to give it up when we were born. He immediatly liked the dresser type bikes and bought a Suzuki C50T. He really enjoys riding the bike and has put probably 2500 miles on it. But after telling people that he bought a bike they always ask if it's a Harley, when he tells them what it is their reaction ranges from disapointment to disgust and at that point they treat him like a second class citizen, so he's already decided he wants a Harley. I talked to him about it and even though he's happy with his bike he still wants one. I think it's a shame that he cares that much about what other people think. Strange because he's a very smart man that started a business from stratch and has done well in life, paid for his house, cars, etc in cash.
I think that where I have the biggest problem with Harley, it has more to do with the mystique, the image, the perception than the actual ride. Plus I feel like they've sold out and watered down the brand by selling dog clothes and stuff like that. It's almost like teenagers the way the Baby Boomer Harley guys try to fit in, always wanting to have the latest and greatest to show off to others and try to feel like they "fit in"