These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Anvilicious: The series, especially the books, seem to suffer from this.
Crowning Moment of Heartwarming: "The Enchanted Square" is about a blind little girl named Billie who is given a Raggedy Ann doll which comes to life and shows her how to "see" with her imagination.
"There's some who see with the eyes in their head, and there's some who see with the eyes in their heart."
Ensemble Dark Horse: The Camel With the Wrinkled Knees appeared in only one book, but was so popular among fans that he became a major character in the movie and TV series, even one of the Fleischer cartoons.
Harsher in Hindsight: Shortly after the success of the Raggedy Ann doll, Johnny Gruelle's daughter Marcella was vaccinated a second time by her school without her parents' permission. The needle was contaminated and Marcella died from the infection in her father's arms when she was 13. Every Raggedy Ann book has since been written in her memory, "Marcella: A Raggedy Ann Story" being the prime example.
Purity Sue: Raggedy Ann could definitely qualify as a particularly saccharine example of this trope. But that doesn't make her any less endearing as a character.
Tear Jerker: The song based on the character. "I'm just a little girl, I'm Raggedy Ann, falling apart at the seams." The YouTube video of a live performance hits even harder.
Values Dissonance: Marcella has a mammy named Dinah who shows up on the "Raggedy Ann and the Washing" chapter, which may be uncomfortable for present-day readers. She also had an explicitly stated mammy doll named Beloved Belindy, who, while positively portrayed, was still very racist and creepy looking.