Hi Mama5 :)
I can absolutely relate to your story. My daughter was born with a tongue and lip tie, and was only able to latch with a nipple shield. She got both of them removed, which was when we tried all sorts of methods to wean her off.
She never was happy with any of them, and was only happy when she was feeding with the shield. Looking back, I could've tried a lot harder to wean her off them! My midwife said that some babies are just happier with the shield, and as long as she's gaining weight and happy, that's the main thing. So I successfully breastfed my daughter until she was just shy of 20 months old, with 100% use of a nipple shield :)
It's a pain in the ass, especially when you're out and about, but it allowed me to breastfeed, so I can't really complain!
So I guess I don't really have any tips of weaning, but I guess I wanted to say that it's 100% possible to have a successful breastfeeding relationship, with a shield :)
Good luck and feel free to message me with any questions