Re: When do I pump now?
I think OCD could work to your advantage here, as you transition from pumping to nursing. Can you get your hands on a professional grade baby scale, one that is accurate to the 1/10th of an oz? The LC might have one available for rental or know where you can get one. Wth the scale, you can do before and after nursing weights, and by subtracting the before from the after, you will gain a very accurate reading of how much your baby took in while nursing. If baby drank around 2-4 oz, then there's no need to supplement and pumping is optional. If baby seems hungry, you just put him back on the breast. If baby drank less than 2 oz, and is acting hungry, then maybe you want to give him a bottle and then go and pump.
A lot of what you're seeing is normal. Babies often require just one breast per feeding, and it's common for a baby to feed in just 5-10 minutes, particularly once he has become an adept nurser or when mom has a high supply.
Coolest thing my big girl said recently: "How can you tell the world is moving when you are standing on it?"
Coolest thing my little girl sang recently: "I love dat one-two pupples!"