Breastfeeding

This is baby #3 for me and I haven’t been able to breastfeed in the past. With my first, my supply didn’t come in until a week after Baby was born and I was super young (19) so I just didn’t try hard enough. With my second, he had some health issues and I was unable to attempt breastfeeding while in the hospital and by the time we got home my supply had dried up and baby refused to latch. I reallllly wanna try to breastfeed this baby, but I honestly have no idea where to start. I’ve always been a “don’t force it if it doesn’t work” kind of person, so I never put myself through trying too hard with my first two. If anyone can give me tips, I’d appreciate it! These are my main concerns:

My milk supply is not very good. It takes a while to come in and it dries up very quickly once it does. I’m assuming this is because there’s no baby latched to keep the supply up, but I still feel like it’s going to be an issue if I can successfully get baby to latch.

Getting baby to latch. I have VERY small nipples. So small, they are almost inverted. Are there options to help this? I heard nipple shields can help, but I’m skeptical- they are so small I feel like even in the shield they wouldn’t reach. Is pumping my only option if baby can’t latch because of this?

Thanks for any tips or advice, and please don’t judge me for not being able to before or not trying hard enough. 😔