I had a similar discussion to this last night with a few people. One was a girl (I won't say woman because of the immature attitude) and her friend who was looking to get a bike. He is caving in to her "I won't speak to you if you buy anything but a Harley" even though she's said many times he has no chance with her.
Now, the real fun thing is that the ones that give me any real problems about the fact that I ride a Boulevard are the passengers that can't ride at all. The people that actually RIDE the bike are of the attitude of "It's 2 wheels and it keeps up with our bikes." You put my bike side by side with my buddy's Heritage Softail Classic and unless you look for the logos, you can't even tell the difference, except I get better mileage and I have water cooling so I don't have to worry about mine overheating in traffic jams in the summer. The guy that has the softail has said several times to me, "You got a bike that runs with mine, looks like mine and at 1/2 the cost of mine. Now that's a deal." He's even admitted that the fabled "Harleys keep their value" is utter nonsense. He went to trade his in on a Road King and they would only give him 1/2 what he paid for the bike..which was still more than my bike cost even after taxes, tags and accessories, but he's lost 10 grand on that bike where if mine was traded in, I'd lose about 5 grand of value.
Another good example is helmets. One of the passengers won't let her husband buy anything but the Harley branded helmets. Now, these helmets are made by another company and they just stick the logo on the back. I've priced the identical helmet from the original manufacturer and it's 50% less cost. To me, a logo is never worth adding 50% to the cost of something, be it bikes, accessories whatever.
Harley makes a good bike...it's just not worth the extra money for the name.