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I think the newest evo you can get is the way to go. I have a 91 evo that has been awesome. Having said that my friend had a 96 evo that was way smoother in every way. Both have been really reliable.
1996 Evo Ultra ! Beat on that bike, modded the motor with cam etc, put a ton of chrome covers on it (which I won't do now causa hotter new bikes) then ran it thru hell and high water on road trips. Ran like a top and traded it for my 2010 Flhx...It's still running strong as far as I know. Great motor !
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.
Slideshow: Harley-Davidson's challenges aren't abstract; they show up in dropping shipments, shrinking dealer traffic, and strategic decisions that aren't yet translating into growth.