And I try to get in as many pumps as possible, but am already doing 1 after morning feed, 2 during work day, and one after his night feed (not after the 7pm feed, but closer to 10pm, to get as much milk as possible before I go to bed).

I think there may be a solution here - pump after the 7 pm feed (say half an hour after) and around 10 if you can.