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More windings around the post better sound?

When I was younger, and playing pro, I didn't cut my strings, I just bent them into all kinds of crazy shapes after winding the right amount and let them spring around. Looked cool on stage, and I got good life out of them. As I got older I cared more about clean lines, less about zig zag string windings looking cool. So I bend then cut and put the bent part into the hole in the tuner.

But yea, nothing wrong, tone wise, with not cutting them, as long as they are not going to come off the tuners and the downward pressure, assuming you're on a fender style headstock, is present.