I've never understood Harley's. It's gotta be emotionally driven because I can't see anything rational about them.
There's no real performance for the cost and size of the engine. There's certainly no economy.
Style is subjective but the same exact style can be had in a Honda Shadow for example for a third of the cost and you'll have performance and longevity exponentially.
One of my all time favorite bikes was a VMax. Smooth as a sewing machine, not bad on gas if you stayed out of the throttle but oh God if you did get into it, it will set the asphalt on fire. All with very little maintenance.