Super depressed because of painful breastfeeding experience

I feel so down and can't even enjoy my baby boy. I'm constantly stressing about not being able to breastfeed. I've seen lactation consultants and multiple midwives who've said the latch is fine, but my nipples tend to look flat after a feed so I feel like the latch could do with some work. It hurts so much when he feeds but I love holding him and feeding. I try to do it once a day and just feed through the pain. I got the silverettes, nipple shields and weleda nipple cream but they don't seem to have helped. I've just been guzzling formula and expressed milk down his throat so he'll stop crying but I really wish I could breastfeed him at least a few times a day. Does anyone have any advice? Does the pain go away eventually?