I asked my dad this once (He rides an 08 FXDB) *For him anyway* He's always wanted a Harley (He used to have a 73 Sportster he rebuilt) and despite there being better choices, he just likes it.To him the appeal is, It's not the fastest, It's not aerodynamic and it's damn sure not efficient, it doesn't cut through the wind, it shoves through the wind.
That's a summary of what he told me, I wouldn't place him with the average HD rider either--he rides his bike every day to and from work and on the weekends, and doesn't buy into the whole (HD Lifestyle) they sell, He calls the folks who buy into that crap, posers and wanna be's the real bikers are the ones who are just riding, not putting chrome everywhere and buying it for a LIFESTYLE.
So I guess it's a matter of choice and preference really.. While I personally wouldn't own a Harley, I would be a liar if I didn't admit his bike put a smile on my face, the Low end torque was fun.
ALSO, Not to mention modern day Harley's are damn near maintenance free. *Hydraulic valve lifters so you don't need to worry about Adjustments*
His bike has 50K Miles and nothing has broken on the bike..yet