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No need to swap bearings on an 08 front. First year for the Brembo brakes and 25mm axle. Only need to change out an ABS bearing if needed. Rear wheel has to be 08 and earlier though so it limits your choices if you want them to match.
 

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No need to swap bearings on an 08 front. First year for the Brembo brakes and 25mm axle. Only need to change out an ABS bearing if needed. Rear wheel has to be 08 and earlier though so it limits your choices if you want them to match.
I believe you can only use a 08 rear wheel on your bike without making modifications. 2008 was the first year of the rear wheel compensator or cush drive as it is sometimes called, the 07 and earlier bikes do not have this feature and even though the 09 and later bikes do have the rear wheel compensator the compensator rubbers are a different design and the wheels are wider, to make any 09 and later wheels work you would need a wide tire kit installed on your bike. You can make the 07 and earlier wheels work but you would need to change axle bearings and rear drive pulley. You should be able to find some nice wheels that are made just for your year bike. There is also wheel exchange companies out there that take the stock wheels and chrome them, I got the 08 Street Glide chrome wheels on my bike and they look great, I got them from chrome exchange, chrome wheel exchange, wheel spacers, Harley chrome wheels, Harley trike wheels, trike wheels, hub saver, harley wheels
 

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The bare rear wheel is the same from 02-08. Brake rotor, bearings and pulley are different on the 08 but will bolt on and press in the older rear wheels. We put both my 08 wheels on my buddies 05 using his rotors and pulley and a set of 08 axles and nuts.
 

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The bare rear wheel is the same from 02-08. Brake rotor, bearings and pulley are different on the 08 but will bolt on and press in the older rear wheels. We put both my 08 wheels on my buddies 05 using his rotors and pulley and a set of 08 axles and nuts.
The rear wheels are not the same because the 08 has the compensator housing casted in the wheel, the 02 -07 wheels are the same. As stated you have to use the 08 pulley and 25mm axle and bearings to make it work on older bikes. But I think the op wants to put a wider wheel in the rear.
 

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I put a 18 off an 11 on my 08. My 08 was non ABS so I got a non ABS wheel and it bolted right up. No issues.
 

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The rear wheels are not the same because the 08 has the compensator housing casted in the wheel, the 02 -07 wheels are the same. As stated you have to use the 08 pulley and 25mm axle and bearings to make it work on older bikes. But I think the op wants to put a wider wheel in the rear.
Your 08 and my 08 must have been made differently. The IDS pulley on mine was completely bolt on. The rear wheel carried the same part number from 06 (when it was introduced) to 08 on the SG rear wheel. And the 08 SG rear wheel is happily living on my buddies 05 Ultra with his original 05 pulley and 05 brake rotor bolted on. We elected to replace his axles with 08 ones as I had recently replaced the bearings in the wheels I traded him. I also had an 08 Ultra Classic with the same bolt on IDS pulley on the original "wagon wheel". Wider rear wheels will definitely require some "modifications"
 

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Your 08 and my 08 must have been made differently. The IDS pulley on mine was completely bolt on. The rear wheel carried the same part number from 06 (when it was introduced) to 08 on the SG rear wheel. And the 08 SG rear wheel is happily living on my buddies 05 Ultra with his original 05 pulley and 05 brake rotor bolted on. We elected to replace his axles with 08 ones as I had recently replaced the bearings in the wheels I traded him. I also had an 08 Ultra Classic with the same bolt on IDS pulley on the original "wagon wheel". Wider rear wheels will definitely require some "modifications"
That's correct the 08 pulley bolts on to the rear wheel compensator then the pulley/compensator assembly mates with the compensator pockets that are molded in the rear wheel. Just as long as you use the complete assembly then you're OK if you use a 08 rear wheel on earlier models. There isn't any problems with the front wheel fitment.
 

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That's correct the 08 pulley bolts on to the rear wheel compensator then the pulley/compensator assembly mates with the compensator pockets that are molded in the rear wheel. Just as long as you use the complete assembly then you're OK if you use a 08 rear wheel on earlier models. There isn't any problems with the front wheel fitment.
Guess we will never agree on this one. Both of the 08 bikes I owned did not have any pockets molded into the rear wheels. Just a flat surface with tapped holes. The IDS bowl bolted to the wheel, then the rubber wedges and IDS pulley slipped into the bowl. That same 08 rim now has an 05 non-IDS pulley bolted to it and is rolling down the highway. On a side note, I changed the stock 66 tooth IDS pulley out for a stock 68 tooth IDS pulley from a Sportster to overcome some of the loss of first gear torque that was an issue with the 07-08 six speed trans on both my 08's. Relatively simple mod that made the bike much more user friendly here in the hills. On the bikes I've worked on, the first year for the wheel having part of the IDS system molded as part of the wheel was 09, along with the wider swingarm and 180 rear tire and multiple frame changes.
 
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