Harley's problem, at least among my peer group, is twofold.
1: Price
2: Perception
For what you're getting, Harleys are, in general, just too expensive. For years now, they've sold "freedom" and "heritage". Those work fine for the older crowd that has been their main market for the past 40-odd years, but it doesn't resonate with people my age. Most of my friends are on modern supersports, sumos, and a few are into vintage bikes like me. The hipster chopper wave is cresting, but they're all built off actual old MoCo products.
I actually rode a 2018 Fat Bob and Forty-Eight special. I walked away underwhelmed. The transmissions shifted very nicely, as good as any Japanese bike I've been on, and the brakes were outstanding, but handling and power were both lackluster.
I have noticed they aren't really promoting their smaller 500-750 "Street" models. Those are in the 6-8k range, which is actually pretty reasonable for a new bike. Beyond that, they're just too expensive.
Second, the attitude. I don't buy into the Hell's Accountant shit. The bar-hopping, t-shirt and no helmet wearing, slow cruising mentality just doesn't do it for me. I don't think I have any friends my age who that appeals to either. I'm more interested in packing miles on the odometer than seeing what new pre-distressed tshirts the Bar and Shield is rolling out this quarter. I don't own and ride motorcycles to belong to a community or brotherhood. I do it because I enjoy it. I enjoy the experience, I enjoy the tinkering, and I do it for the ride, not to try and build an identity for myself. I feel like that's what HD has been doing for years, trying to get customers to build their identity around a Harley. And it's just not working anymore.
That said, I'm actually kinda excited to see their ADV bike in the flesh. I'd have one, just because it's weird and different. I'm hopeful that electric bikes take off, and the Livewire sells well for them. I was thoroughly impressed with the Zero I rode, and would gladly have one as a no-maintenance commuter if I could justify the price.