Re: Now a supply issue -WHAT ELSE?!
I would wake him, too. You can do a "dream feed". You just pick him up and offer your breast by rubbing them on his lips. He will wake up enough to nurse, but won't really be fully awake. Try to do that at least once during the night rather than hooking yourself up to the pump. He will stimulate your milk production better than the pump will.
Is he fussy and acting like he's still hungry after he has nursed for 10 full minutes on each side? If he seems satisfied and is sleeping well at night, I think he's probably getting enough. You can try Mothers Milk Tea, oatmeal (pure oats, not instant) and increase your foods rich in vit. B.