So we are pregnant with our second child. First pregnancy/delivery/breast feeding was a huge failure.

I am wondering if it would be worth purchasing a breast pump this time round?

What did other people do?
Same with me. I went to the hospitals breastfeeding refresher class. When in hospital I engaged the lactation consultant to talk through the issues I had and we worked on a plan to overcome the issues I was going through. A week after having bubs I had a follow up one on one class with the LC. I also called the ABA a few times. I never purchased or hired a breast pump because supply wasnt an issue for me. I did use nipple shields for the first 4 weeks due to attachment issues and damaged nipples but weaned DD off them. DD is now 14 weeks and all is going well.