I had low milk supply for the first month and a half for various reasons (I had a C-Section and my milk was slow to come in, my son needed formula for weight gain, he was a sleepy feeder and fell asleep the second I went to nurse him, my hormones made me nauseaus during the second week of his life, I didn't nurse him frequently enough becuase he slept a lot and I wanted to demand feed and also, I was slightly anemic). Blah! Trying to relactate was an emotionally trying time - but God is good and I was persistent.
Originally, I would nurse him, then use a rented hospital grade double breast pump after each feed. This was so stressful for me because I could never tell how much he was getting and I felt like I was playing an absurd guessing game about how much formula to feed him afterwards.
Just recently my milk supply dropped because he stopped nursing at night - and with the grace of God, it did come back; however, I tried a different approach this time - it required a lot of pumping...I hope you have some time on your hands.
For about a week and a half straight I pumped (and nursed periodically in the morning to see if my supply had come back up). I noticed that if I pumped every hour - I got more milk than if I pumped every two hours. I would pump while he napped - until I got enough to feed him (approx 3.5 oz give or take an ounce or two). When he woke up, I would feed him what I pumped. This way I was relieved to know that he was getting enough (no less than approx. 20 ounces a day), and was stimulating my breasts to produce more milk.
Night pumping is really important for stimulating prolactin levels. I have read that between 12-3am is the most important time to nurse or pump - but I have also heard that between 10pm-4/5am is also a good time to increase prolactin levels.
I also took Fenugreek throughout (up to 24 of 610mg a day )- and although I could tell a difference once I started making more milk, I couldn't really see much of difference during the relactation process. I also have a perscription for Domperidone, but have never used it.
Side note: I have since changed my diet - no caffeine, no cow's milk, lot's of oatmeal with molasses (high iron), no tea or soda. Why? I discovered that tea (not herbal) interferes with iron absorption, cow's milk has a lot of calcium, but not enough magnesium for proper calcium absorption - the phosphorus in soda also hinders calcium absorption. I take cal/mag/D supplements (not everyday), Iron supplements (not every day), prenatals (daily), B-complex (daily), Prenatal Omega-3 (daily)
Nursing is awesome! If you are persistent (and have some time on your hands) you should be able to get your supply back up.
BTW - Medela makes a special flange for larger nipples, so I've heard.