Well,
I am of the video game generation.
I've owned 2 Harleys - both in my 20's BTW.
1. '08 Dyna Glide Lowrider - put about 20K on it.
I had exactly 0 problems. Never leaked, never coughed, never failed to start. 6 speed meant that 80mph was around 2900 RPM if i remember - barely trying. However, 6th gear was crap below 70. It lugged the engine a lot. Handled OK for what it was - something to cruise around on and enjoy the scenery. Rode it to Luisiana and all over Texas. Looked really good, wasn't comfortable for more than 100 miles at a clip.
2. '12 Street Glide - also, put about 20K on it.
I had exactly 1 problem with it. The compensator sprocket started wearing out... in Utah. I rode it another 2000-ish miles (and 7 states) before I got home and had it replaced... within 2 days.... under warranty.
Comfortable and capable. Maybe not Goldwing status (Fred), but pretty darn good. 80mph was around 3200 rpm if i remember correctly (shorter 6th gearing on the touring and 103 models compared to the early 96in Dynas)
Both were great bikes at what they were built to do. That's the honest truth of it. The quality is top notch (these aren't the Harleys of the AMC years). The ride is better than you would expect. I will own another one in the future - i'm pretty sure.
I just roll my eyes when everybody always starts the Harley bashing. It gets old really quick and it's pointless. The truth is: for every serious riding BMW/Honda/Yamaha guy, there is probably a serious riding Harley guy. (There are just a lot more "other" Harley guys in addition) - This is purely my speculative opinion. The Bikes themselves are great. The mass # of the owners pulls the skill level down below average. This is why we all get stuck behind the Harley parades.
If you want the young(ish) guys opinion:
Harley makes an excellent product - it's not designed to do 150mph and carve canyons. It's made to cruise (Hence cruiser) and it does it very well.
I think they are taking a step in the right direction - their marketing has been aimed at mid-life crisis and up people for too long so they've lost the younger buyers over time. The phrase "Get'em while they're young" doesn't just work for cigarettes.
I think there are 2 problems to overcome:
1. The typical Harley "Lifestyle" and "Image" is what the younger generations associate with their parents and older generations. Young people don't want to be like their parents. They will be - they just don't know it yet. Harley would be taking a huge risk to change their marketing/branding away from their main demographic.
2. This is motorcycling in general - not just Harley. Young people in general (my age and down) have been coddled and sheltered too much (of course there are some outliers) to be interested/excited about the "Freedom" and "Excitement" and "Adventure" and lets face it... "Possible Danger" of riding a motorcycle.
Everything was nice padded bumpers, rounded corners, those plugs you put in the outlets to keep kids from shocking themselves and Barney the dinosaur.
The majority of kids my age were raised to not do things without supervision, told that being independent was bad (everybody come join in the group circle and we'll play a game), and that it was irresponsible to do things other than the pre-prescribed curriculum of life and success. - So they don't. You might think this is stretching it a bit... but I lived through it and interact with tons of these people all the time. They don't have an adventurous bone in their body because they were told all their lives that could be bad and instead here's a nintendo. They weren't taught to explore and form opinions, they were taught to listen to directions. (I know this probably seems like a bold faced lie to parents on here, but if you always here them saying "I don't know, what do you want to do?"...
I blame the helicopter parenting trends of the last 30 years. The majority of parents of kids in my generation would never let their angel have a motorcycle growing up - their dangerous (and they don't have padded bumpers and wall socket plugs)
You show me a 20-something that doesn't get off the couch and i'll show you a set of parents who never let him actually figure out anything for himself when he was growing up.
Rant Over.
P.S. I'm only on the couch on this lovely Friday evening because I threw my back out earlier this week. The muscle relaxers might have something to do with the mess written above
... Guess I'm not all that young anymore.
P.P.S. Get off my lawn ...Just practicing