Thank You, Thank You, Thank You
Thank you to everyone who took the time to reply. I'm literally overwhelmed by the responses. I needed the perspective that you all gave me - it's so hard to keep that when it's late in the evening and you are tired and frustrated.
So.... the little boy is off the bottle until we get this all figured out. The LCs helped me with his positioning/latch and although it's not comfortable, it's less painful. He nurses great during the day - in fact I was delighted to find during my last session at the support group that he took in 4oz from my breast, which totally destroys my theory that he could take more from the bottle than from me!!!
He has also had phenomenal weight gain - over a pound in the last week and a half.
Night times and evenings are definitely more challenging - he will happily hang around for an hour and be still rooting after an hour of sucking/snoozing. I like the suggestion about getting music going/trying to make the feeding sessions more relaxing for me so I'm not focusing on having him finish up so I can "move on". It's important for me to remember that THIS IS MY MAIN JOB RIGHT NOW!!!
It's definitely looking up - thank you to everyone who reminded me that I just need to give it time. I guess this has probably been said a hundred times but I was just beginning to feel there was something wrong with me that something as "natural" as breastfeeding was reducing me to tears a few times a day.
Again, I really appreciate everyone who took the time to write. I really had no idea that being an EPer would be so hard in the long run, thankfully I have you guys around to put it all in perspective.