LHG, are you talking about a Spanish, an acoustic, or what?
There are acoustic/electrics where the string must be passed from inside the body, and Spanish strings have to be knotted loosely onto the bridge.

I was just rereading a guitar book that recommended (for acoustics)that you wrap the string half around the peg and feed it through the hole from outside the head, which means that you would preset the hole 'across' the neck.
I put a little tension on the string by holding it 'up' with my 3rd and 4th fingers and 'down' with my first finger at the frets, putting a sort of kink in the as-yet unwound string. This gives enough slack for about two turns around the peg when tensioned.
And one at a time, as I was taught.