You said it so much better than me but exactly the same! Teardrops On My Guitar was my introduction and since then I’ve been obsessed.This sums it up so well for me too. I grew up with each of her albums and they each kind of define different chapters of my life for me. When each album came out, I was the same age as she was when she wrote it....she always felt like a girl I went to school with or something, especially in the debut era.
She has always had such a gift with writing songs that perfectly depict and describe different relatable experiences and emotions, to where you feel like she's a friend going through the same stuff as you are. That kind of emotional connection through music is rare, and that's something that's given her such staying power...her audience has grown up alongside her and has felt seen through her songs. Even as she's become a huge star, she's (mostly) still conveyed universal human emotions/experiences through her music to where she feels like your peer.
For me, the only time it truly felt like she was a huge out of reach star was a lot of the 1989 era. Which was fun, but different. Even with reputation, where she had a bit more of a put on character/"image", she was spending much more time chatting with fans online under the radar than she was in the press and it made her feel closer to the fans in a way.
She's grown up the same time many of us have, has made mistakes and gone through things...but it's really cool for her to be at a place now where she seems so comfortable and happy just keeping to herself and using her craft as much as she wants in a much more grounded way.