I live in milwaukee (home of HD) and I have seen it all. This is my opinion:
Its a simple issue why harley engines don't make power, they don't have the RPM capability to make power, their engines overall design was never designed to make more then 70 WHP stock, most of their "bigger" engines are nothing more then big bore kits on the same motor, they are air cooled, etc.
Harley is ingrained in so many peoples minds here that anything other then harley is no good. Either its "Jap crap", that "victory HD knock off", or a "wanna be". They actually do have a point though, harley has created and maintained a fleet of large engined v-twin bikes that are the most copied bikes on the planet. They are the authentic v-twin cruiser simply because they are the only surviving v-twin manufacture from the dawn of the 1900s. You look at most import bike manufactures and most will copy a lot of what HD does, however they never get it right. A good example will be the street glide, there isn't a single bike out there with hard boxes that duplicates the look of the SG. Too many "copies" don't look porportionaly correct (too wide of boxes, the body lines don't flow, etc) and they don't get the quality of the paints/chrome right. However this isn't fair to the "copies" because they are not charging 24K TTL out the door for a kawasaki vaquero, Star venture, ETC. If those cost that much money there would be a lot more to spend on the fit/finish/etc.
Where I feel harley went wrong is they refused to innovate at all, and gave up. The problem is their whole catalog has become stale and it could eventually lead to their downfall. If you eliminate the VRODs they have essentially just put big bore pistons on the same old engine and called it something new for longer then I have been alive. Sure they added EFI (to a engine that was designed to be carbed) and they are starting to put brakes that work and good transmissions in the bikes, but they haven't had any innovation since the VROD, and look how old that is already.
What I flat out don't understand is why harley wont build a street glide or similar bike with a 1,700 (or bigger) CC engine based off the Vrods Rev engine. Tons of Guys spend 4,000$ to get 110hp out of the 103s, or upwards of 8K on a 120R swap, so nobody can even argue that there wouldn't be a market for a box stock street glide with 140 tire hp and a that much torque stock. I am 100% positive if they came out with a CVO with 160HP stock out of a bad ass new motor, it would be the most demanded/desired harley at the dealership. I have brought this up amoungst harley owners here and the 3 answers I get is A) the power isn't needed (yet these guys have 4K+ to boost power of their stock bike) B) The motor wouldn't make the low end torque they wanted and be too reliant of RPM for power (Which they would have a point with the stock Vrod motor, but a larger newer engine wouldn't have that issue) and finally C) It would not be a harley. I think they wont come out with such a bike/engine simply because it would make all of their older bikes and parts irrelevant. 100% (without the VROD) of their bikes/dealers rely on the 4K to 10K worth of upgrades people buy just to get anywhrere from 100hp to 140hp. Who would buy a 120R motor and upgrade parts/install for 6 to 8K when you could just sell your bike and buy a stock harley with 150 to 160 hp stock?
The reality is my money is loyal to who makes the product I want, and I desire the best out of what I want. If harley made the rocket 3 I would own a harley. Of course if harley made the R3 it would have to cost 45K because it would be better then their CVO bikes that already cost 35K+ out the door. Which brings me to my next point. Ever notice how when ford owned jaguar they made completely garbage cars that were nothing more then rebadged global platform cars with garbage parts at a high pricepoint? Notice how once they were sold that all that BS mostly went away, and that they are making cars that are actually "competitive", visually stunning, and massively powerful? Ford wouldn't let jaguar be the car company it could have been because of idiot decisions and not wanting to compete. The same thing could be said of harley, they are so land locked on a particular formula and making the choice to avoid any modernization that it will cost them just like it almost killed jaguar. People said some things are forever, take Jack daniels whiskey for example. Well as popular as whiskey is, it could (and will) fall out of popularity for other drinks. And you look at the fact even Jack is making their whiskey with honey and other extra mixers. Its clear that they had to innovate to stay in buisness, even when they are the most well known whiskey (and brand in general) in the world. If harley doesn't innovate and continues down their path the name will start to become irrelevant, and thats the main thing they have going for them. Its also the main reason victory has fought a uphill battle as a younger company. And indian will likely fail/have a very rockey existance since the Indian company has never been a well known standout brand, and has been completely irrelevant for over 50 years. Same reason importing the holden monaro and commadore as a pontiac GTO and G8 was stupid. Take good cars only to call one the same name as a infameous american muscle car it looks nothing like, the other a "g" series (which relates it to the awful G6), and put them under a name that synomous for garbage, and what will you get out? Simply put harley has had a very rocky existance and almost went belly up numerous times, and the next one wont be too far away. The import companies are starting to "go their own way" with a lot of models and are eating more of the market share up.