Simple answer, but it takes a lot of words to get it out, so go make yourself a sandwich, take a wizz, then settle in for story time
For me, it's not about "mine is better than yours" and never was. I have had a hard-on for Harley since I can remember, and over this past year, I have test-ridden several in a desperate attempt to get one for myself that "fit" me and my needs.
Let me start off by saying that I'm not a slave to labels. I don't buy anything for status, I buy what I like as long as it fits my needs and I don't care about price as long as I can justify it to myself. There are some seriously awesome Metrics out there from Suzuki (M109R), Yamaha (Star Warrior and Stryker) and others, so today you have more choices than ever before. Quality, reliability and power.
I don't buy into the whole "heritage" BS that Harley owners all fall back on. If I wanted true American Heritage, I'd look no further than Indian, which has more than H-D does. BUT as much as I love the Chief, I don't feel it is worth $32,000.
First Harley I ever rode was the anti-Harley... the V-Rod Muscle. Loved it, almost bought it. Next was a Softail Nightrain. It was sluggish, harsh ride, and felt like I was riding my couch. I decided to go with my Hammer S over the V-Rod for the more useable power band, better handling, and easier riding position.
Last week I took out a Dyna CVO (08 FXDSE) and while visually I believe very few bikes can touch it, it rode like crap. It rattled, shook and felt like it was falling apart. This was a $30,000+ bike when new, $20k on the used sticker. Brakes were downright scary and barely stopped the powerful 110 motor-powered bike. I got off and cursed it. Well... once I found the damn kickstand... which you need to be a detective to find.
Toay, I went to ride a Fat Bob and Road Glide (both 2011's). There were many things I liked about the Road Glide, but for one of the largest bikes on the road I was shocked that it was so cramped for both the rider and passenger. A Ducati Streetfighter has more legroom. Vibration wasn't AS severe, but it was there, and after a few traffic stops, it was annoying. My wife got vibrations even at 70mph cruising, especially in her floorboards. Power was anemic, but the handling was really quite nice for such a large bike. But for a $25k bike, it should feel like a quality bike IMO.
My Hammer S is super smooth, hardly any vibrations, has more power has better brakes (dual disc Brembo) and turns heads because it doesn't look like every other bike on the road. At some point most Harleys blend together as a blur honestly. Harley will bob a fender, paint everything black and VIOLA... a new model!! When it's the same old Dyna we've seen for decades.
The Fat Bob was what I thought would be "the bike" for me. But then I couldn't get over the rear fender. It is the same fender you'll see on a 50 year old Harley. It's the same brakelight that reminds you of a Kaiser VW from WWII. The suspension is overly stiff for a bike that's not made for pure performance, and again... it nearly rattle teeth loose.
I also own a sportbike, so I know about giving up certain degrees of comfort for performance or a particular ride... but on a cruiser like I've been looking at, I should not need to sacrifice comfort.
Right now Triumph and Victory are bringing the heat. Lower prices compared to H-D, comparable models, more power, more 'factory options', and they are getting better by the year. Problem is that Vic has a crappy dealer network. Too few, and too far between. I'm also not a fan of buying a brand new, premium priced motorcycle at a lawnmower shop. Though I did visit Bike Town in Ohio last week.... they sell only bikes, and are dealers for both Harley and Victory. Oddly enough, the service bay was PACKED full of over 30 Harleys and not one single Victory. Simple fact.
Victory has a sterling reputation for overall reliability across all the models over the years. Harleys do not, we know this. Our most common problem? Clutch cables breaking, that's about it for widespread, repetitive issues. H-D has many, many more... and more severe.
So while I still like the Road Glide I rode today, it would take about $2k in mods just to make it rideable for me, and another $4k in mods to be "cool" and tailored to my wants & desires. If I bought a Ness Cross Roads or Crosscountry, it would come the way I want at the same price, and I'd add maybe another $3k-$4k in mods to customize it. And after all that... the Vic would still be smoother, take sweepers harder, have much more torque, and not look like half the other bikes I pass on the highway.
IMO H-D has become the "me too" bike. And I'm not a "me too" kind of guy. I respect H-D, I like a lot of their bikes, and I cannot ignore the draw to them... but ride them back to back, and you'll see why so many Harley owners made the switch to Victory. Even the hardcore like Sonny Barger and now several other Hell's Angels.