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Cut the nail in half, insert into drilled holes using 90 angle adapter on your drill.
Drill the big holes, finish the wood, drill the small nail hole the size of the nails using a 90 degree adapter, insert the half nails in those holes.
All of these methods sound pretty cool, but why doesn't someone simple make a heated, expandable coil that you could insert into the pipe, turn it on, and while it's heated properly, bend to a desired shape?
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