I can relate to some of this. It took my baby 6-7 weeks to be able to latch without a shield. At the time, it was all I could think about and so hard to get through. Honestly, in retrospect, I wish I hadn't spent so much time and energy trying to make breastfeeding work. What I didn't realize is that now that he breastfeeds, we're at square one of a different challenge. At 12 weeks he has started preferring breastfeeding and refusing bottles, which would be fine except that his latch isn't effective enough for him to eat enough if he just breastfeeds. I also developed an oversupply from all the pumping so I still have to pump regardless and am prone to clogs. It's been incredibly stressful and I wish I had just stuck with what was working and spent more time enjoying my baby. This is super individual though, so your case could be totally different! Just thought I'd share from the other side of things in case it helps at all.