The one thing I learned from a restringing video from Taylor a couple years ago, is that using the distance to the next tuning peg as to where to put the bend in the raw uncut string is a good place to start to keep from getting too many winds on the peg/post. He shows this at about 4:45 into the video. I do the bend, not cut

Sidecutters on the pins, I don't do that, I use the little fork in the business end of the hand winder I use.

I've always re-strung string by string, to keep tension on the neck about as close to fully strung/fully tensioned as possible.

Having a mess of un pegged strings there seems like a hassle.