Pretentious is the key word because they saw themselves as the “thinking person’s music site.” In the early 2000s, they were known for mostly reviewing indie rock music, with a glancing acknowledgment of hip hop. Once they realized that niche alone wasn’t going to pay the bills, as guitar-based music had increasingly fallen out of favor throughout the 2000s, they started trying to take pop more seriously. But you’re right: even as late as TS’s 1989, they didn’t deem her work worth exploring until Ryan Adams came along and validated it.
Slate nailed it a few years ago: their mostly male staff dismissed pop and mainstream country because their audiences were strongly female. And Taylor wasn’t seen as “edgy” enough for them.