Harley has a lot of problems for a lot of reasons.
The old bikers want nothing new or innovative. The V-Rod (a Willie G baby) as an example, was completely shunned by the Harley buyer at the time of release. Problem is the old biker market is shrinking fast now.
Yes and no... every Harley rider I knew (including me) who took a ride on the Vrod hated the bike (horrible seating position, slow handling, and the disc wheels on the first year caught every cross-breeze and truck wake eddy), but loved the motor. More than a few of us were ready and willing to put down money right now, on the spot, for a touring bike with that motor. What caused Harley to insist that no, the only place that motor would be offered was the painful styling exercise, is totally beyond my understanding.
As for the old bikers... yeah, this has been a problem since I got my second Harley, an FXRT (rubber-mount Super Glide with streamlined fairing and bags originally intended for the Nova), in 1983. Hadn't owned the bike two weeks before some geezer muttered something about putting a Honda fairing on my Harley. Now, of course, there's an industry in making replicas of that bodywork, as the California cruiser crowd has decided they like it.
I also had the experience of going to a Harley shop to get standard Sportster parts for my tube-frame Buells and getting a load of crap about how that's "not a real Harley." Yeah, I guess not, 'cause it'll leave your $20K CVO in its dust.
Everything the least bit outside-the-box (FXRT, XR1000, a whole lot of "sport" models, Buell, the stillborn "Street" 500/750, and now the Pan Am) gets the stink-eye and "that's not a real Harley" muttering from the old geezers. Luckily these guys are dying off, so the Pan Am might yet stand a chance (the dealer in Boise sure had a lot of them, and I saw a surprising number while we were tooling around the Northwest for the last few weeks).
Include in that they don't make an affordable motorcycle anymore. One of the main reasons RE is exploding on the global market. Great value for the money. Can HD say that? Especially now that some Brainiac decided to ditch the Sportster. That was by far, my favorite Harley.
The Street, though nice bikes, were a complete failure. They're "damned if they do, damned if they don't" now, and have painted themselves into a bad corner.
The Street bikes were dead on arrival because Harley's upper management foolishly announced them almost a year before they showed up in dealerships. That gave the old farts plenty of time to make it clear the bikes would never, never, never be considered "real Harleys" before anybody ever actually saw one in person. They then doubled-down on the stupidity by product-placing a couple on a TV show: "Blue Bloods," whose median viewers were something around 70 years old. Didn't help that the Street bikes were pretty forgettable, though they did a better job of styling the radiator than just about any bike I've seen.
One good thing about the Street models, though: the front brake caliper from the first couple years fits a Himalayan 411 and provides a noticeable improvement in stopping power.
I've had a number of Harley's and have wrenched on a ton of them. I liked them all, for different reasons (I simply love motorcycles, regardless of brand).....but I can't see one in my future anymore. Too big, too heavy, and WAY to expensive. They had what I call the "Cadillac Attitude". It doesn't matter what lands on the showroom floor, people will buy it because it's as Cadillac. That wind that was filling HD's sails for a long time, has stopped blowing.
I'm an American. Of course I don't want to see Harley fail....but they've done this to themselves, and the last guy who ran it didn't help in the matter from everything I've read. Unfortunately, the only thing that lasts forever is herpes.
My 21-year-old Road King, just back from the Northwest (didn't qualify as the "Northwet" because we had exactly one day of rain in a 24-day trip) with 118K on the odometer, is probably my last Harley. We did an almost 5800-mile trip, but I'm having trouble two-upping on this 800 pound bike. It's fine once we're moving, but starts and (especially) stops are inelegant, and I can see that my days of two-up cross-country trips on this thing are numbered--and I am NOT going to get one of their $40K Rascal-Glides (for one thing, I can't afford it). When we move to trailering a mid-size bike to someplace like Maine or Colorado and taking day trips, the bike will not be a Harley. Their only "middle-weight" bike, the Nightster, combines the terrible ergonomics of the Vrod with styling that makes me long for the Street 750.
I think the best thing that could happen to the Motor Company is to be taken private, either by a group of motorcycle-enthusiast executives (as in 1981), or by a "white knight" billionaire who sees the potential to make money in a shrinking market by making bikes specifically for North American riders. I know people who'd love to buy "American" but don't want anything in Harley's current lineup.