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Road King 2003 Classic 100 Year

If you are referring to the primary cover gasket, it's not difficult. Just keep track of the different length bolts that go in the cover and where they go.
Best bet if you aren't sure is to take a piece of cardboard and draw the primary cover on it and push the bolts through the cardboard in the proper position.

The riders floorboard and rear floor board should be removed too.
 
My brother has a leak in his primary Gasket. Should I try and replace this myself.

Make sure where the leak is first. Remember that when the bike is on the kickstand the primary drain would be the lowest point, therefore if you are leaking from the mainshaft the oil would run down to the primary. I would wipe the primary first then let it stand for a while to make sure. If the leak does appear when the bike is parked, and there is a wet mark behind the inner primary, then you'd need special tools to get the race off as well as the pulley nut. I would then replace all the seal to include the quad seal.
 
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