| The direction of the winding matters if you have a 2+2, inline 4, 4+1, inline 5, etc, etc, headstock configuration for your tuners. The pegs on the headstock turn in opposite directions depending on if they are top or bottom so as to properly wind the strings.
Peg hole diameter is the size of the actual hole cut in the headstock wood. You'll need to buy tuners for that specific size hole, unless you feel like drilling bigger holes (you aren't going to go smaller on the same neck though...)
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"It's one of the great fallacies, it seems to me," said Lee, "that time gives much of anything but years and sadness to a man."
- Steinbeck, East of Eden
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