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I can't speak for the wire strings, but I am sure there are plenty of methods used by guitarists with those very same machines.
For the nylon I have taken to using a technique employed by classical guitarists, I use this on regular pegs as it is very simple and fast.
Basically you feed the end of the string through the hole then bring it around the peg or roller and twist it around the string a few times. Then wind the peg which secures the twist. No knots, very fast, and easy to remove when that time comes.
Carrie, what I do is exactly what I do with metal or soft strings on upright posts on banjo or guitar, but it's 90 degrees off. I don't know what you mean by "uploading sideways". The only "uploading" I know about is in the digital/computer/internet realm.
So for the treble side I point the hole toward the bridge and pull the string through all the way. Then I guide the end of the string back toward the post *along the inside edge*, guide it *under* the part of the string between the nut and post, and pull the string back towards the wooden part that runs the length of the headstock. I hold it there with a finger of one hand and with the other hand I tighten the string (sometimes with a string winder). Very soon the part that went under is locked. After that I can let go and turn until the string is in tune. Then I clip the string. On the bass side I do the same but the direction toward the middle is of course opposite.
Thanks Joel and Jody.