SY,
It can be troublesome to pump. I couldn't agree more. With latch-on, the bb tends to prefer one side and the other side which is neglected will have a 'shortage' of milk.
Also, if you are letting the bb latch-on, do try to alternate. For eg, the last time the bb drank on the left side, start on the right side the next session. Otherwise, the breasts will be lop-sided.