It sounds like you've been over and over what happened with your DS and you're using it to try to see how you could do better next time around. You know of a lot more of the perils and pitfalls that you found yourself in last time, so take that on board as information, but try not to let the emotional aspect play on #2.

Firstly, you've identified that he had a high palate that wasn't diagnosed. So you couldn't have done anything about that. Next time around, baby might not have that problem, but even if they do, you'll know enough to not put your nipples through 10 days of hell before it's found. So hopefully you'll avoid the damage. Everything else stems from the initial problem, as you've described it here. It's not uncommon, you just got very unlucky and didn't heal well.

So next time around, I'd suggest you join the ABA. Now, before you give birth. They'll be holding an early daze or bfing education class in your area probably before your baby is born. That will help enormously in setting you up to establish bfing correctly. They also have information to help you overcome any challenge that might come along. A LC is great, have you thought about talking to one of the ones you saw (if you felt they were good) before birth as well?

Another thing I'd say is if you develop any of the signs of infection next time around, get onto them early and don't wait. Do you think you can identify the early signs, so you don't have to wait until you're really sick? I unfortunately had mastitis more times than I care to remember (dodgy ducts from oversupply) and I learnt what the very early signs were, got straight onto it with ice packs after feeding, anti-inflammatories and into the GP ASAP. My GP was very good with her bfing knowledge (bf three children herself and had attended a conference on mastitis just before I showed up with it, lucky for me!), but if you think you weren't diagnosed quickly enough (particularly with the staph infection), think about finding another GP.

You might also want to look up baby led attachment (there's a great clip on you tube, might even be on here). That can help establish correct attachment from birth.

GL, hun.