I visited with an IBCLC nurse and found a few helpful suggestions. She had a "My Brest Friend" pillow that I really liked, so I just ordered one today. I still have to add a pillow under his head, but I liked the way he didn't roll forward towards me the way he does with a Boppy. Also, she suggested a steroid/antifungal cream (nystatin/triamcinolone) for healing cracks (she didn't think the nipples were infected and suspected that overuse of the APNO may have been causing irritation). So I have been using that during the night; you do have to rinse it off, and during the day using coconut oil to keep nipples moist (drying them increases the pain when the dry skin deforms when he first latches on).
I do experience vasospasms that are also painful. The IBCLC nurse suggested Vitamin B6, as some mothers find relief. I also take ibuprofen if it's hurting bad. I notice them happening more after a painful feed, less with feeds where there's a good latch.
Also, I've been working on propping him with lots of pillows. He forms a good latch most of the time. Sometimes I still experience him pinching or smashing the nipple, always on the right (today was a bad day for this, but yesterday was perfect). I don't think this is due to a forceful letdown, as this breast produces less than the L and I don't hear him gulping when he smashes the nipple. He can make a good latch and have a good feed if he wants. I'm trying to figure out what, exactly, changes this. So far, no luck, just trying to make the best of it and hang in there. I'm starting to feel more hopeful about breastfeeding.