Questions about switching from pumping to feeding directly at the breast

My little guy is 5 weeks and started out bottle fed breastmilk due to being born almost 4 weeks early and some less than ideal nipple anatomy. We are working with a lactation consultant to transition him to the breast but I wanted some other perspectives. Any and all tips are super appreciated!

How do I balance pumping with directly breastfeeding? Do I replace a pump with a nursing session? He takes longer on the breast than at the bottle, even with a premie nipple and pace feeding. We suspect it’s because he’s taking little breaks on the breast due to it being so cozy and warm! He also takes breaks on the bottle but not as long.

How do you know when to switch sides?

We are using a nipple shield for now due to baby not recognizing my nipples even when they are in his mouth. Any tips on when/how weaning off of the shield works? I’ve started with the medala but just purchased the lansinoh to try it out. Do you have any brand preferences?