Winding acoustic guitar strings

1. How many times should I wind my guitar strings?
2. Is there a wrong way to wind guitar strings?

How many times should I wind my guitar strings?

Anywhere between 2-4 windings will be plenty and, so long as you are restringing your guitar in a conventional way, this should ensure that you have enough tension in your string to maintain your tuning and avoid any string slippage.

Is there a wrong way to wind guitar strings?

Consequences of stringing the wrong way

Don't wind the string on the wrong way. ... Not only will you have to turn this tuner the 'wrong' way to tune up, the angle out of the nut is sharper and the string can get fouled or run against other tuners (neither of which is great for tuning). Don't do it this way.