When I pump I massage my breast first to "loosen" the milk ducts. It just helps my flow better. Once the initial amount is pumped out I go back and massage my breast again, especially the base area of the breast. This again will release the milk better for me and I usually can get more milk out. Also, I use a medela pump. Not all pumps are created equal so that could be part of your problem.
Also, a suggestion for your friend and her milk supply, you might suggest that she take fenugreek. AFter my last baby my doula recommended it to help increase my milk supply and it really did work well. It helped bring my milk in more by about 1/3 the amount. You can buy this at any nutrition supply store and I know HyVee at 156th and maple carries it too.
As for yourself, it sounds like you need a complete hormonal work up to find out your prolactin levels. There is a doctor here in Omaha, Dr. Hilgers with Pope Paul VI group who specializes in infertility and treating women with pcos. I know women who go to him with this very problem and he's helped them to concieve. There might be other doctors who have been trained by him who can also help you.
Good Luck! and KUDOS to you for helping your friend out! Most people wouldn't do this.