I'm not sure about your supply & expressing - I'm sure someone else will be able to advise you there.

But, I wanted to encourage you about the breastfeeding thing. My DS is 10 weeks old & BF'ing only stopped hurting last week. (I know, 9 weeks seems like ages away - but it's gone really quickly!!). Firstly, with the bleeding nipples, it would be a good idea to see a LC & check that your attachment is correct etc. Once you know that everything is working properly, it's easier to ride it out - knowing that it will get better (sometime around the 8-12 week mark - according to the experiences of my other BF'ing friends).