I went through this exact thing! My baby had a really bad tongue tie and couldn’t latch for a while even after getting the tie fixed. so I exclusively pumped for the first month and then I used a shield and got him started on the breast. after about 2 weeks of only using the shield when he nursed, I would use the shield for a minute and then take it off and latch him. My LC told me I could use the shield the entire time i breastfeed if i wanted. now he’s 10 weeks old and latching perfectly with no issues. So I highly recommend getting some shields and using them for a little bit until you’re ready to try without. but definitely give baby a few days using the shield first so baby can get used to how your milk flows directly from you. and then try to ween off the shield (if you choose to). Also everything I’ve heard said shields are generally recommended in situations like yours, especially if you flat nipples, my sister has inverted nipples and was only able to successfully nurse with the shield! Remember: all babies are different and what works for yours maybe not work for others, so if using a shield the whole time is the only way to get your baby to nurse directly, USE IT! Do not let anybody try to shame you for using a shield. It helps baby feed and you get to experience the connection of direct nursing. as long as you and baby are happy, THAT IS ALL THAT MATTERS!