A.C.
I also had milk supply problems--was supplementing with 17 oz of formula per day but little by little the supplementing has now dropped to about 4 oz of formula per day. I was able to increase my supply by only having to wake up once during the night to pump. During the day, I'm able to breastfeed as much as he wants because I mainly work from home--not sure if you're working. (My son is 12 weeks old and has been sleeping about 9 hours/night since he was 7 weeks old.)
Anyhow, here's what I do. I never go more than 5 hours without pumping at night. If his last feeding is well before I go to bed, then I pump before going to sleep. Based on when I think he will wake up, I set my alarm to wake up usually between 3am and 4am. I saw a lactation consultant, and she said that regarding the prolactin levels, the best time to pump is between 12 and 5 am. She also said not to go more than 5 hours without pumping if trying to increase supply. Thus, what I would suggest is to pump before you go to bed since this would maximize your sleeping time before you have to pump again. Then set your alarm for 5 hours later just in case your baby doesn't wake you up first. I find that it's easier to wake up my son in the morning compared to the middle of the night. Thus, if the 5 hours have passed, wake your baby up for a morning feed. Like this, you are only getting up once in the night to pump rather than twice. It's worked for me; I hope it can work for you!
Best of luck!