not sure if i'll be any help. But my midwife said that you can start leaking milk from as early as 16 weeks! Not sure why one side would be leaking more than the other though. Maybe you're laying on it differently and squeezing it out or something in your sleep. I only started leaking around 35 weeks, but it doesnt like pour out or anything, thank god! I don't think it matters if you start leaking milk early or never at all during pregnancy in conjunction to having problems breastfeeding. Just some people leak and others don't.