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To me it would depend on how much value he places on a brand new bike with 2 year warranty, the confidence of proper break in and maintenance, better brakes, better ride with IDS, more fuel capacity, bigger engine and a smooth six speed. If I were paying 5-6K more for that maybe not but would I pay 3-4 more, probably. I have 6500 trouble free miles on my 08 with 18 more months of warranty!
I don't think either one is a bad choice. 06 is a great bike. But pay 15-17k for a low mile great bike... or pay 18-19k for a great bike with all the things mentioned above... particularly the warranty...
The only way that would work for me is if I could get the 06 with low miles for around 10-12k. Those deals are out there... but are few and far between.
I went to the Harley dealer and they had the right color RG w ABS and time I put 103 , cams TP and all I wanted it was 30k with interest I said fine I will give you 2k less ,would not even counter offer . I walked out found a 04 the previous owner had dropped 40k on for 15k and bought it they are out there. I'm talking 95 w 203s, wide tire kit ,Baker dd6, performance machine mags w metzs ,performance susp.( no air shocks), the 08 frame connector, oil temp gauge and a pickup of spares SWEET! THEY ARE THERE
The 2008 96ci motors have more torque in their stock form (other than the addition of at least good flowing slip-ons) than the 88's will ever have without at least cams or a 95 big bore kit. They are smoother at highway speeds. The 08s have a 6 gallon fuel tank (about time too) and in my experince with my 08 FLHR, it is significantly more stable in fast turns. I mean it handles better than any previous year Harley I've owned. Neverowned aSportster so I have no comparison for them. The six speed isn't a bad thing either. My 08 FLHR with the custom baffled Fuel moto rush mufflers, a SE air Cleaner and PCIII will flat run away from my friend's twice dyno-ed 06 FLHT with SE air, a SE race tuner, and SE performance mufflers. My mods investment is under $700. His mods investment, about $1200 with the dyno time. Mine still hasn't been dyno tuned as I'm running the provided Fuel Moto program. Yeh, his bike is a little heavier but I outwiegh him by over 70 lbs, so that's not making the difference.
And as mentioned above, there is the 2 year 24,000 mile warranty and the fact that you get to break the new bike in the way you think best and not purchase someone else's oil burner or worse.
Make a list of all the things you want on the bike and then search ebay, craigslist and such. You may find exactly what you are looking for and save big $$$$. That is what I did. I totaled up 6K is receipts.
Effective May 25, 2008 at 11 AM, I made my first HD bike purchase at Simi Valley HD Dealer (that I highly recommend and ask for Andy and Craig). I bought a 2008 Vivid Black Road Glide with ABS, security, cruise, and cast wheels. I love it!!! Have a safe ride...
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