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lay the fender on the tire with an appropriate spacer, such as 3/8" fuel line taped on top of the tire ( like you see on the build off tv shows)
now eyeball it.
are you happy with the look ?
does the arc of the fender match the arc of the tire, wheels and rotor- or does the fender look squashed- and if so ,do you care.
if so you may want to look at getting a new fender and hitting the catalogs. ( or the popular fatboy fender or HD street stalker fender, which mount with adapter blocks.
if all is good, you can mark the positions for your new holes.
use brand new drill bits
pad and secure the fender so it can't spin if the drill bit grabs ( or get a Pal).
tape over the location with masking tape.
drill through quickly, do not let heat build up-
you choice is try a small bit and then go bigger- I prefer using a big bit and doing it once, making sure that I am centered on the mark
Is this for a stock fender? Are you sure you need to elongate the holes? I had my 21 with stock fender and didnt need to do it. Now if you do, your only talking about moving the rear of the fender up a very slight amount. Like mentioned earlier you only need to elongate the hole. Use a bit that is slightly bigger than the hole that is already there. No need to drill a brand new hole.
Our Tech likes to use a dremel tool to elongate the existing hole. He finds that the safest approach to prevent damage to the fender. Or tape around the hole and use a 3/8" drill bit to hog out the hole.
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