Have been to quite a few concerts in recent years where artists celebrating an album's anniversary actually go out on tour and play the entire album from start to finish. There's probably a few songs from POY that Jewel hasn't played live for years and years (I'm just guessing here), so could be intriguing if she decided to do something like this.
I like the idea of a re-release, but tbh I generally don't buy these unless there's something really, really worth having that's previously unreleased. I'm not sure a simple remastering would get me to part with my cash as it's not an album I really listen to much these days anyway. There's likely an audience for it though, especially those who stopped following Jewel's career after that debut record.