Ugh! First of all, I am sorry that you are having to go through all of this. It must be even harder because you are not at 100% yourself.
The fact that you said breastfeeding was extremely painful leads me to believe that you probably had an incorrect latch, where Emily was probably latched on to your nipple only. That is EXTREMELY painful! It takes a lot of practice for both you and baby to get a good latch, so don't be discouraged and think that going through excrutiating pain was the norm for nursing. And don't think that because you have large breasts that you will not be able to nurse. The baby doesn't have to get the entire areola in her mouth, just as much as she can. As long as she is opening wide and her lips are flanged around the areola and not sucking on the nipple only, that should do it. A lactation consultant can definitely help show you what a good latch is. And yes, even with a perfect latch, it can be a little uncomfortable for a week or so, but it should not be excrutiating.
What kind of pump do you have? Sometimes really lousy pumps can be very painful. I would highly recommend a rental hospital grade pump (ex. Medela Lactina Select) with dual attachments to get back to pumping. You're going to need something really high quality like that to re-establish your supply. And start at the lowest possible suction speed. Do that for a minute or so, and then gradually increase the speed at your comfort level. With a hospital grade double pump, you shouldn't need to pump for more than 15 minutes.
As far as pain goes, I think that it just takes time for your nipples to toughen up. I used Lansinoh, which seemed to help. You can also soak a couple of tea bags in warm water then apply to your nipples. Also, colostrum has incredible healing properties so you can express that and rub it into your nipples as well.
I hope that everything works out for you. Breastfeeding was not easy for me, so I understand where you are coming from. It took me about a month before I felt comfortable with everything. It doesn't always hurt, so take heart in that
DS-Evan, 7/19/2003. PE at 40 weeks