How do you know if your baby is getting enough milk at each feed? I know.. wet diapers etc but is there a way to tell of they're satisfied?

My baby has always had a bad latch to the point where I would cry bc it was so painful. I went to a lactation consultant she suggested a nipple shield and just continue trying until baby grows and latch becomes bigger...so in the meantime I decided to pump and supplement with formula bc of the pain. However pumping seems to have gotten monotonous and I find I can't always pump when I need to leading to more supplementing and uncomfortable engorgement while out for hours.. I'd like to try and get my baby to breastfeed when we are home since I'm with him all day and only supplement when i need to when I'm out or not around and my husband can feed him.

I've only been able to get him to latch between 5 and 15 minutes on one side..he hasn't been able to latch on the other side I don't know if it's the positioning or what. I still feel like he needs a bottle afterwards of 2-4 oz... which makes me think that he's not actually getting enough even though he's either falling asleep or pulling off.

I'm having trouble breastfeeding and pumping because it makes my nipples super raw and irritated so I can really only try to do one or the other. However if he doesn't feed well I get super uncomfortable want to pump and get frustrated bc I'm too sore to try breastfeeding at the next feeding time and it becomes a cycle..

I need help and advice please!! At a loss and don't know what to do .