At some point they killed themselves with the myopic nature of metrics. understanding the average rider age of a harley led them to start investing in motor homes and golf carts assuming the market was going to vanish underneath them. At the same time, the Milwaukee managers froze the plant in time out of sheer terror that any change would drive away their customers. in the 80's the "engine sound" patent was recognized which only nailed Harleys other foot to the floor.
Harley still ran on a chain primary drive by 2007...the last car that ran on this was the Packard in 1930. The only innovation that came to this was plastic guide shoes to replace the old metal ones out of a cost saving effort that basically empowered the transmission to kill the bike after 20,000 miles.
Management went completely deaf. in 2001 the death wobble for Dyna's sold to the california highway patrol was ignored twice by the company, and once proven by CHP riders on a closed course, the company begrudgingly issued a parts fix but no recall, and no replacement. Harley in 2010 still had single crankpin, inlay type piston rod engine made largely from pot steel iron that pushed 650lbs in their smallest sportster motorcycles. They were failing a plurality of foreign emissions controls for both noise and air quality but didnt seem to care. 33 years ago most managers remembered the tariff they lobbied government for, and how it saved harley. They expected another one.
comparatively they were getting crushed by better bikes. Japan had double crankpin, liquid cooled, fuel injected, balanced and computerized engines that outlasted harley davidson by hundreds of thousands of miles and ran on low maintenance solutions like belt drive and shaft drive that didnt need service for 100,000 miles. Even japans air cooled monsters like the Yamaha Raider 1900cc in 2006 could idle comfortably in 100 degree summer heat...something Harleys largest models that were still 300cc's smaller could not achieve without shutting down a cylinder and entering "parade mode"
Harleys v-rod, their only new design, came from Porsche, and their new exhaust came from a consortium of other motorcycle manufacturers who offered options and techniques for compliance. They desperately want to get out of the manufacturing business and into the 'branding' business. Sure, the milwaukee 8 is a nice new engine, but at 40-50 grand for a new dyna glide, harley still misses the point.
Gone are the boomers that will drop that kind of money. I'll go for a Honda Goldwing which is not only more powerful, but more reliable and cheaper, than a new bagger.
Harley arguably isnt a motorcycle company at all, its desperately trying to just be a household brand. Better US motorcycle companies like Victory and indian (polaris) exist with modern double overhead cam design, liquid cooling and keyless start to name a few features, but victory learned the hard way what it means to go toe to toe with a brand that exists as a living anachronism.