When did you start pumping...?

MrsJerseyJets

I am a STM and tried BF with my first and had a lot of issues so I gave it up pretty early on.  This time I am trying again and things seem to be working out better, so my question is--when did you introduce pumping into your routine?  My baby is 5 days old, my milk came in full force about 1.5-2 days ago, and my baby is doing pretty good at the breast right now but is so tiny that she is not emptying out my breasts at feedings.  It is fine right now, but I also have issues with breast tissue under my armpits that back up and make it hard to move my arms (part of the problem with my first), and my OB told me with my first to pump after feedings to make sure I get a lot of it out to relieve the problem.  

This time I want to try to do things right, so I don't want to introduce pumping too early and have an oversupply all the time.  I will, however, need to get all the milk out at some point before it becomes a bigger problem.  What do you suggest as far as pumping?  How much longer should I wait?  Since my milk just came in days ago I want to hold off to let myself regulate the supply a little, but I know I can't leave it too long or else things will get painful if my LO doesn't start emptying them soon.  Or do you think that she will start being able to feed enough to empty them?

Sorry for all the questions and confusion...I really want to try to do things right this time and BF for the majority of the time before I go back to work.  Thanks for any advice you may have!