I loved this set- they're so adorable and the collection teaches a lot of techniques. That said, I wish the kit came with guidance on the recommended order; I started with Olivia which was not the right call! If you've never crocheted before, I'd recommend starting with one of the super basic Wooble kits before this set (like Pierre or Kiki).
My recommended order: Sidney (you could possibly swap her with Clint since it's a lot of the same skills required); Clint (he's a lot easier than he looks; I'm not sure why he's rated as Beginner+); Olivia (different techniques than most beginner woobles); and lastly Jade (definitely an Intermediate; keeping track of the right place to put each stitch is a challenge!)
Some feedback for the Woobles team: I wish the "semi-flat" sewing technique for Sidney was demonstrated in one of the videos; I figured it out, but it wasn't intuitive as a beginner. Some of the videos felt like they skimmed through important steps and that the reference videos weren't very helpful since they showed pieces that were radically different shapes than the pieces in this set.