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02 I feel is the best year, had the timken crank bearings, mine still has carb. Really other than cosmetics increased gear not a whole lot changes in the Harley lines, if you can take care of your bike and change things that wear the older ones are just as good or better than the newer.
I had a 2006 FLSTC and was very happy with it.
Now I have a 2009 FLSTC and no complaints there either. Not sure about the 5th gear wine, never noticed it, and now I am gear driven so that adds a hint of a wine regardless of which gear. Nothing that bothers me though.
And I change the handlebars from the get go so no idea what the originals where like lol
I have an 08' I never got any noise in 5th, but I use to get a clatter sound in 6th. I put Spectro 6speed transmission oil in, and clatter gone. Very smooth now... I love my Heritage.
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