I am someone who rode cruiser and touring bikes exclusively until about 2.5 years ago when I bought my first adventure bike I have been riding something for 20 years now (Sheesh!!). In that time frame, I looked at HD and was so incredibly unimpressed with them, I entirely don't understand the following. Compared to the competition, HD are hot, vibrate a lot, under powered, slow, poor handling, high maintenance, and said maintenance can be difficult (belt change), and yes I test rode plenty. If HD was a domestic auto maker they would have been long gone. I started riding a moped when I was 15, then at 16, an old beat to hell Honda Shadow 500, That became a 1998 Honda Magna, then a Victory Kingpin, followed by a Victory Vision, before turning to Victory I was eye balling Goldwings. When I was still single I bought a second bike a Buell Blast for a get around town bike, it was awful and unreliable, that became a Victory Hammer S, which became an A990 which was slightly more reliable than the Blast, that finally became a S.Tenere.
Now with a 10 week old in the house, and daycare payments at $1000/month for cheap daycare, I sold the Vision and kept the Tenere. My only slight regret is I didn't discover Adventure riding until just a few years ago.
I get riding, I just don't get the HD thing. They are just another bike manufacturer.