You can try showering or rubbing a hot cloth on your lobes. This makes them less prone to tearing, and it will soften the skin. Using lubricant can also help the jewelry slide through easier, if you don't have a lubricant you can try vaseline. Most importantly though just give it time, a little day by day, that will also help the healing process...Hope This Helped In Some Way and Good Luck!
I've never stretched my cartilage, but when I skip sizes with my regular gauges i'm guessing it's almost the same, no, but kinda. o.e I just put olive oil on the piercing & jewlrey.
I think putting a clear "base coat" on before the color is supposed to make it stay longer, but I don't know if it really does
I don't know much about peircings, but maybe numb it with ice or soemthing.
Cartilage doesn't stretch, you will have to get a dermal punch.