How bad is this...
#1
Still on training wheels
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How bad is this...
Do I need a new wheel or is there something I can do about this?

#3
post-ironic
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Really depends on how deep the gauge is. Can't really tell from this photograph. Rims these days are made to be really light, meaning they are pretty thin. A deep gauge could cause a rim to break while you're riding, which is never a good thing.
#4
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Looks like a scratch, sand it smooth so it doesn't cut at the pads. You don't have to make it disappear, just so it isn't sharp. Looks like a hole above it.
#5
Still on training wheels
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Not sure... I hit the brake this morning and heard the harmonious melody coming from the rear break. Stopped and saw that 
The dot above is not a hole but one of the tire nubs that I caught head on.
I am going to try sanding it and see what happens. It does not look like it is deeper than the wear-dots, but we'll see. Any one else have any ideas?

I am going to try sanding it and see what happens. It does not look like it is deeper than the wear-dots, but we'll see. Any one else have any ideas?
#6
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Crisis averted. Sanded smooth and all is well again! Thanks guys!