I think this is actually HD's goal at this point; to become an expensive boutique brand and reduce production to increase demand. The golden years of the early to mid 2000's are pretty far in the rear view mirror at this point, when they were moving a quarter million bikes a year during the age of easy credit. My impression is that their target market is going to be buyers who don't really care about the brand, but do care about the status of owning a bike that costs 40 grand and up. Even when the vehicle market crashes (and that's inevitable) and prices drop, I suspect Harleys are going to stay extremely expensive. I have serious doubts about how well a marketing strategy like that will work out, though. Luxury brands like Mercedes, Bentley, Porsche, Ferrari, etc all have the status of either class, performance, or wealth, or a combination of all three. People who don't really know much about cars will still see a Mercedes and think "ooo look, rich guy driving by". Or they'll see a Ferrari and think "man, look at that awesome machine, must be nice to have all that money, bet he can't even drive it". I don't think people have that perception when they see a Harley, even if they have some idea of what a Harley costs. Harley has spent 50 years cultivating that image of "born-to-be-wild badass biker", and that's not going to be an easy transition to "Oooo look, a Harley, that guy's probably a Fortune 500 CEO with a supermodel trophy wife", or "look at that amazing high tech performance machine". If I'm a well-off guy who has the disposable income to spend 50 grand on a motorcycle, I sincerely doubt I'd spend it on a Harley, a bike that's legendary for its image of being owned by either gang members or else roleplaying orthodontists.
I think the intersection of the sets of "people who have a lot of disposable income and want to buy status" and "people with money who want a to pay 50 grand for a Harley with the rep of an old man's bike" is going to be pretty small.