Good question. Every little kid thinks MacDonalds is the king of hamburgers. But people who have been around a while and eaten a few burgers know a big mac is really a pretty lousy burger. Same with the Harley.
The Harley is a very primitive motorcycle, very heavy, very stiff handling, very expensive, very underpowered. Todays 883 sportster is the exact 40 horsepower of the 900 knucklehead from 1930. A tiny 250 ninja at half the price will own that 883 sportster and get 80 mpg doing it. Harley's biggest baddest $41K bike with all the expensive screaming eagle parts added on can't even begin to do what a $9k 600 sportbike is capable of right out of the box.
Imagine a car from 1930 with 1930 performance and still manufactured today, but selling for twice as much as a top of the line Honda. Hey I would love an antique car or motorcycle from 1930, but I don't want to buy a new car or motorcycle for twice the money, that has 1930 performance.
While other companies have been working to reinvent the motorcycle, harley invested in Madison avenue. They advertise very heavily and just keep selling a bike that they haven't bothered to change much since high tech was a wind up record player.
When I was a kid I absolutely lusted for a 1200 superglide. Later after owning several great but much cheaper bikes I could finally afford one. Took a Superglide for a test ride, and it was by far the worst bike I had ever been on. Very primitive and vibrated like a jackhammer, lots of engine noise, lots of transmission noise. junk. It really is one of the worst motorcycles at any price.
But the thing is, you have to decide if you think of motorcycling as a sport or a lifestyle. If you wanna be part of that social biker scene, dress up in assless chaps and a doo rag and hang out at big bike rallies then you really want a Harley, you won't have status in that crowd if you have a better cruiser that doesn't have the harley name attached.
Unless of course you buy a Victory. A better made, superior performing, more American cruiser.