Leaving aside some of the poser owners, I still think Harleys themselves are OK. Some have a nice classic look to them.
That said, they're too bloody heavy and very underpowered. Standard pipes sound f!$%ing s!$% (HD put the same mufflers on export bikes as are required in the most stringent countries) so you usually have to splash-out on replacements. Changing the air intake is now a f!$%er too due to various sensors and EFI (can't just stick in a bigger jet these days). The suspension is f!$%ing terrible too. I've had a good number of HDs and, without fail, the main think that lets them down is the ride. It's Showa front and rear but they're built down to a price and that's as f!$%ing obvious as it is primitive. Other gripes... Well, the wheel hub chrome just fell off and looked s!$% in no time. The wheel rims (made in Japan, Italy and Taiwan) have s!$% chrome too. I bought spare wheels of eBay and had them powder coated with stainless spokes. Expensive but it looked nicer. What else? The seat stitching used to let in water so it'd blow bubbles after a wash. Removing the rear wheel on my Road King was a PITA. Setting the belt tension when refitting the rear was also a PITA, as was setting the headstock bearing tension with an unreliable 'fall away' method they use.
I test rode a Rocket III once and it was a magic carpet in comparison to my big block HD. The brakes were much, much better too. Still, the paint on a HD is jolly good. I'll give them that. And the motor's easy to work on.