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I voted NO also. I wouldn't be hung up on it being a anniversary bike. What about a Heritage or Deluxe instead. Last year of the deluxe. I doubt any recent HD is worth more used than it cost new.
Like others have said if you feel the need poll folks who dont know you then its probably not the bike for you. On every bike Ive purchased I knew ad soon as I saw it I wanted it and the opinion of others never came into consideration.
As to the thought of flipping it for a profit because only 2500 were made, that is highly unlikely. I have a 2008 105th anniversary WG one of only 2000 made for the last year of the bob tail WGs before they were redesigned. I bought it because I like WGs and wanted to keep one around.
I can assure you it will not resale for anymore than a similar low mileage, showroom clean WG despite having a badge that says 0217/2000
A Harley is not any kind of investment. Nor do adding pipes, chrome, windshield, different seat, bags add anything. I dislike hearing 'it's worth $x plus because I've invested this much in my bike', no you didn't invest anything in it you spent money on it. Don't forget you have to register it, tax and insure it, get it serviced, replace tires too. It's a toy. Buy the toy you want to ride but don't think you'll get any profit back on it because you won't. It's depreciating from Day 1.
If you think it is an investment, you need to study finance more.
It is one of the few new bikes I like the looks of. Thst being said, both the front and rear tire are so wide that the handling has to suffer. To some people, it is hardly noticeable and to others its a deal breaker.
If you like a blacked out bike but want one that handles better, the Low Rider S is a better option.
If you want the best value in a new bike, the regular low rider or softail standard gets you a lot of bike fir a modest price.
7 Surprising Harley-Davidson Products that Are Not Motorcycles
Slideshow: The bar-and-shield logo shows up on far more than motorcycles, some of the company's most unexpected products have nothing to do with riding.
Slideshow: From the troubled AMF years to modern misfires, these bikes earned reputations for reliability issues, questionable engineering, or disappointing performance.
Crazy Bunderbike Build Looks Amazing, But Is It Impossible to Ride?
Slideshow: The Swiss custom shop has taken a Harley Softail and stretched it into something so long and low that it looks closer to a rolling sculpture than a conventional motorcycle.
Engraved Rebellion: Inside Bundnerbike's Glam Rock II
Slideshow: A standard cruiser becomes an intricate metal canvas in the hands of a Swiss custom house known for pushing Harley-Davidson platforms far beyond their factory brief.