I pretty much fit that demographic, well minus the style. And Harley has mostly gone off my radar and really was only on there before because of Buell (I loved the City X). There have been one or 2 Sportster variants which looked kinda cool but still weren't bikes that I'd buy myself. I also read up a bit on the "H-D Street" line and I'm happy at least that they're trying, but it will likely take awhile to change their image. My real hope is that electric bikes give them the ability to experiment more and push some innovations which could get younger people more excited about their bikes.
I was just writing about how it would be interesting to see how they could blend the Harley aesthetic into a modern city bike and then it hit me that they might be the best company to be able to pull it off. Retro is obviously in right now, people want to go back to the past but with a modern twist. And their name, style, everything is that retro motorcycle look for most Americans. It would be a real challenge design wise to make it all work and seem "right" but if they could get it to work that would grab my attention.