I don't think you could go wrong with any of the recommendations above. Start with his 3 studio albums, then move on to Band of Gypsys and First Rays, then check out some rarer live or studio outtake stuff. Yeah, the sound quality isn't the best you've ever heard, but it's good enough. The songs should always be more important than the sound, and his songs are top notch. His studio albums (although the second 2 in particular) are also quite influential in that Jimi was one of the first guys to use the studio as another instrument to make sound, through effects and such.
I can't speak of the reissued Are You Experienced vinyl, but it's definitely worth picking up if you can find an older version for a reasonable price. I always think it's fun to hear an album exactly as it sounded when it first came out, especially an album as important as that.
