Ahhh excited for you! I agree, go in order and opt for the remasters of Little Earthquakes, Under The Pink, and Boys For Pele. They sound incredible. Just a note that those are deluxe versions containing b-sides and performances from the era. Earthquakes ends with the title track, Pink ends with "Yes, Anastasia" and Pele ends with "Twinkle." Then definitely keep going chronologically and dive into From The Choirgirl Hotel. I would give anything to discover it this way! I heard it after To Venus and Back (my first Tori album), so I was already used to her electronic exploration. Had I heard Choirgirl first, it would have 1. knocked me over with the sonic shift compared to the first three albums and 2. make me appreciate Venus even more, where she doubles down on the plugged sound - which yes, then do To Venus and Back next. It has a live disc featuring tons of songs you'll have heard and a few introductions to fan favorite b-sides. If you like Earthquakes-Venus, I'd say you're a fan and you can start exploring the patchy latter half of her career. There is absolute gold on the 2000s-2010 albums but the she takes some wrong turns, ones she's even alluded to. Check in with us throughout! It'd be great to hear what you're enjoying and what you're not.