Do any of you guys listen to her really old stuff? Like from the early 90's? I've never; I don't even know where I could find it much less buy. It would probably be super dated and maybe even horrible

I think maybe from Junior Sweet (her best selling album) from '97(?) is when I could tolerate the dated-ness.
That's around the time she actually gained popularity I think... from the Swallowtail Butterfly era.