I'm actually kind of the opposite - I lusted for a Harley when I was in my pre and early teens; riding around on a Honda CL100, I wanted to be an "Outlaw Biker", join a M/C -- the whole works. As I got older, I realized I couldn't afford a new Harley, didn't have the patience to rebuild an expensive basket of junk parts, and had started getting into Musclecars (specifically old Mopars).
So, I left Motorcycling for about 6 or 7 years.
Getting back into Riding again at ~22; I "re-entered" with the purchase of another of my Moto-Lusts: an '89 Honda HawkGT. The First (and I still have it) of a line of oddball Motorcycles I would own and ride.
From there, it's all been downhill; I fell in with a Moto-crowd of eclectic tastes and varied interests, some of whom actually owned Harleys, and got to ride some of the OTHER Moto-Lusts of my youth -- and was totally underwhelmed. Compared to even my lowly Hawk -- to me; most Cruisers with twice its displacement came up wanting.
Compared to many of the other, far more capable bikes I have sampled........ Well, there IS no comparison.
I felt Cruisers were overweight, underpowered (but the vast majority of them SOUND mean and powerful, don't they?), have poor ground clearance, and too much "Blizzing" for my taste.
Plus, it seemed every Doctor, Lawyer, Banker, or company President in the whole feckin' US of A had decided to "live out" my childhood fantasy of bein' "Billy-Badass Bika' " -- which I outgrew, IN my childhood. -- I had no wish to become yet another poseur in a "Sea of Individuals". As one of those eclectic friends of mine is fond of saying; "EVERY day can be Halloween, when you own a Harley!" And it's only gotten "worse".
Now, at the lower-edge of Harley's demographic, I have almost Zero interest in one - OR, their Japanese competition.
I've matured somewhat -- I can see where Cruisers might light someone's fire -- but they're not for me.
The Buell sparks my interest a bit; so much so that I've come THIS >< close to plunking-down money on an Ulysses (the Adv-Touring thing has sort of taken hold on me lately). I love the sound of a V-Twin, especially one that can rev-up a bit (single-crankpin-narrow-vee Cruisers need not apply here!), but an inline-four in full-song also raises the hair on the back of my neck.
Well, it seems I've started ramble-writing The Great American Novel here, so I'll wrap it up.
EVERYONE is different, and they all change throughout life. You can't lump some person into a "Boomer" or "Gen X" or "Gen Y" category, and say "They will only buy hunched-over futbol-fcuking monkeybikes", or "This Generation only likes riding vibrating Gynocological-Exam tables", or "Those ADV-Riders are Nuckin' Futs!".
It just doesn't stick. By and large, motorcycling seems to have a LOT of poseurs (I may even be one of them), and THEY seem to be largely divided amongst Racer-boys and Psuedo-Outlaws. And, you never see either in any kind of inclement (or even threatened!) weather. But the REAL Motorcyclists are gonna ride; and THEIR choice of mount is going to vary - even throughout their stable.
Those who don't give a Shiznit on what the World thinks is the best bike - they just pick something that talks to THEM, and ride the wheels off it - two-year-old bikes with 45,000+ miles is the norm.
I'm ending it now, sorry to subject you all to this sill rant.........