Re: Low supply last time
Congratulations on the baby to come!
I think the first thing to remember is that every nursing experience is different. You had issues with low supply last time, but this time you could end up with oversupply. Don't laugh- it happens! I had low supply with my first and a monster oversupply with my second, in part because baby #2 was a much better nurser and in part because supply tends to improve with subsequent babies (since your body has had more opportunities to experience the hormonal changes of pregnancy which prepare you to breastfeed).
The second thing to remember is that you and your baby want to master breastfeeding before you introduce bottles or the temptation to use bottles into the equation. Nursing a newborn can be super-frustrating, and when you have the option to use a bottle... Even the most pro-breastfeeding parents will sometimes yield to the temptation "just this once".
So I would not pump at all in the beginning. Give yourself at least 4-6 weeks to master breastfeeding, to make sure your supply is more or less in line with baby's needs, and then start pumping.
ETA: I totally understand the fear that comes from having struggled with supply. When I was pregnant with my second, I considered pumping right from the beginning, too, since I didn't want to have supply problems again. And I am SO GLAD that I didn't, thanks to what I had learned about oversupply on this forum. Because the second time, I had oversupply and that was without even having a pump in the house. If I had pumped, as I considered, things could have been much, much worse.
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!"