She did think it seemed low considering how long we were at it, but she said that can be normal with the shield. I did ask her about this but I think it got lost in the shuffle. Her primary concerns are getting him fed via bottle and getting him to latch. I don't think she's concerned with how much he gets at the nipple.
As awesome as she is she's going away for two weeks and is unreachable until she gets back except via email, and I am not going to bug her while she's on vacation so I took Auderey's invitation to keep coming here for help and support.
At this point I am going to backtrack and try for very short sessions and just get him comfortable. I am going to keep him fed via the bottle and not push for latches long enough to be a feeding. I do feel like I know my baby and he's feeling anxious about it, as am I so I think backing off and regrouping and just going for comfort is the way to go at this point.
Oh and she weighed him in his diaper both times so I don't think whether or not he peed matters? But I do believe he did.