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Hello!

I've been saving to upgrade and have seen a lot of nice looking RKs for sale end of this year and I think I'd like to buy now instead of waiting until spring. In the 6500-9000 range.

Are there any significant differences between the 1999 year model through 2005?
I am wondering if a bike with similar mileage and condition is worth $1000-2000 more if it's 2-3 years newer, etc?

Alternately, would I be better off saving over the winter and paying several thousand more for a newer model - 06-09 etc?

Thank you for your input
 

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'99-'05 are all 88" motors and 5 speeds with the exception of the limited edition CVO Screaming Eagle bikes.
They're all basically the same but there are changes over the years, some good some not so good.
Some of the early Twincams (1999- early 2000) had cam bearing issues and all the '99-'05's possibly have cam-chain tensioner problems.
Most by now have been corrected one way or another but a real low mile bike likely hasn't, not all had these problems but it's something to be aware of and find out if a given bike has been checked out and or upgraded.
I'm a big fan of the '99- '02 bikes especially the '02 which many feel is the best year for a variety of reasons.
1999-2002 Twincams had a forged steel lower end with a Timken tapered main bearing set up and a tight end play tolerance, this is what you want for longevity and if you want to build up your HP without worrying about the crankshaft failing.
In 2000 they got sealed wheel bearings, in 01 a bigger rear axle and in '02 better brakes so the '02 has the upgrades and was the last year with the bullet proof bottom end.
In '03 they phased in a cast iron lower end with a flat roller main bearing and relaxed the end play tolerance, most are ok if left stock but if you want more power it's wise to convert to the Timken bearing and have the crankshaft welded and balanced if not a complete forged lower end installed.
This became a bigger problem in '07 when the standard engine was enlarged to 96" via a longer stroke, many had serious excessive vibration issues and some grenade completely.
They did upgrade the cam-chain tension set up that year and it can be retro fitted to the earlier models or you can do like I did on my 2000 and convert it to an S&S gear drive set up and never worry about it again.
The gear drive cams can be installed in the Timken bearing models usually with no problems, the '03 and later bikes often have too much crankshaft end play which has to be corrected first.
All that said if the price is right any year will probably be a fine bike, just make sure to have it checked out by someone in the know or buy one that has been upgraded already.
Again if I had to pick a specific year to look for in that range it would be a 2002 , there's lots of early Twincams out there with upgrades and many with 95" big bore kits installed and cams etc. already done so shop around.
I have 181,000 one owner miles on my 2000 FLHTC,it has a 95" kit and gear drive cams along with a few other goodies like ported heads and she'll run away from the newer 103" bikes and run with the CVO 110" bikes all day long.
Hope this helps, I know it's a bit to digest lol.
Oh and as for '06-'09 the '09 would be the only real step up, they got a new frame and some other upgrades that year as well as the 103" engine although in '07+ a six speed gearbox was added and the 96" engine.
 
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