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The only real way of knowing, is to have a sample tested. However, it's much more economical and convenient to simply change at designated intervals. Oil today is much better and lasts longer that oil of the past. Less fuel contamination is also a factor with the extended change intervals recommended these days.
Even so, these motorcycles run pretty hot, which also breaks down some of the oil components. So, I prefer to change engine oil at 3000 miles. After all, we're only talking three quarts. As such, my personal view is rather than spending money on "High Whiz Bang" oil that supposedly extended your change interval, it is far better to have decent quality clean oil that is changed more frequently.
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.