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You will not regret it! I got my 08 brand new in July of 08 and have ridden it for over 18k miles. The front end is a bit heavier than a telescopic but It handles great!
I would have bought a pre-owned one when I got mine but used ones were actually more expensive than new ones since people were buying them up then putting V & H exhausts or other such mods and then turning around and trying to make a profit by selling them for $2k or $3 k over retail. Fortunately the 09 models rolled out in July and the 08's went on discount. I refused to let the dealer sell me the current year model wich was selling at premium and did not buy until they got me my denim black 08. I rode mine out for $17,800 out-the-door including T+T+T and a nice H-D helmet thrown in. H-D could not match my credit union's rates of less than 5%.
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