I'm on a quest to improve my cotton wicking myself. I started trying the "less is more" approach by starting with a strip of cotton about the width of my coil's ID, but was getting tons of dry hits from insufficient wicking, so I've been trying to increase the amount I use. One issue I was having was that if I tried to jam too much cotton through the coil, it would bunch up on one side, causing the cotton to tear apart when pulling. At the same time, squeezing the cotton to make it narrow I believe was causing the wick to choke. Two ways I found to combat these issues:
a. Smooth the cotton by rolling it (the vid linked by SLIPPERY_EEL above shows a pretty good technique) before threading. Avoid compacting or twisting it; just roll so the outside is smooth but the inside is still puffy, if that makes sense (it should have give in it when gently squeezed).
b. When threading, pull lightly on both ends, keeping the cotton taut, rather than just pulling from one side. This flattens it somewhat and allows it to slide through easier, and allows it to puff back out when released after it's threaded.
The real trick I've found is determining how much cotton to use in the first place. For example, in the vid above, Yosh is using about half the width of the cotton strip, but he's using a 9/64" 22g coil, which is much bigger than say a 5/64" 28g coil. Still experimenting with that.