So I should ask, what should I be looking for when moving the kick slowly through rotation? Just so I have an idea of what to recognize.
Visualize it this way, as you push the kick starter the crank rotates and the pistons move up and down. When a piston is on the way up with both valves closed (compression stroke) you'll feel the compression resistance in the kicker. You want to position the motor so that you're at the max compression resistance for one of the cylinders, then give it a good kick (see below).
A common mistake I see people make is to try to use the muscle power in their right leg to kick the kickstarter. Instead, raise your body weight upwards, straighten your knee, and let your whole body weight move the kickstarter. Note that this is where it gets tricky with older harleys, especially magneto driven ones, because since your knee is straight, if the motor kicks back through the kickstarter it can toss you over the bars or injure your knee.
mystic_1