I was thinking about your posts all weekend while I was out of town, and have just a couple thoughts. Have you experimented with different nursing positions? When my daughter wouldn't latch well, my midwife kept trying to get me to hold her in the football hold (I don't remember why). But DD just flat-out would not nurse in that position and would just cry. I couldn't latch her in the cradle or side-lying positions, either, and my midwife brushed off biological nurturing, too (which I'm SOOO mad about in retrospect). I could only latch DD in the cross cradle hold on a My Brest Friend, wiggling the nipple into her itty bitty mouth which she refused to open more than a centimeter. We did this for about 10 weeks until she relaxed, let me hold her more naturally, and opened her mouth a little bigger (still not great in that department, though).
I remembered there is a picture in the new Womanly Art of Breastfeeding (p. 278) of a mom bottle feeding her baby with the bottle tucked under her arm and holding the baby in the cradle hold, mimicking breastfeeding. The point, I think, is it is a way to help babies accept a bottle. I wonder if it would work in reverse? Like, try a bottle in this position, and then maybe move your LO over to the breast when he's had a little milk and is calm. You could try massaging your breast while he's at the bottle to get the milk all ready to go when you move him over. ???
Many hugs. The other posters are so right, it's totally worth it in the end. It's impossible to have an emotional connection with a pump and a can of formula. For weeks on end, I told myself "you can do this one more time, just one more." I'm so glad I stuck with it. And if, after all, you do end up not nursing, at least you'll know you did everything you could for your baby and yourself.