I just got back from typing this....lol ESSAY in a Youtube comment of all places...but I’m proud of it so I decided to post it here. xD
I enjoyed this movie a lot and think it's more clever and insightful than what others are giving it credit for. But it shouldn't be called "Toy Story 4", it should have been called "Toy Character Study" because that is EXACTLY what it is... I enjoy tf out of character studies and analyzing them to hell and back, so if you're curious, do read on. YES, THERE ARE HEAVY SPOILERS.
Basically, this movie succeeded at what Ralph Breaks the Internet failed to do. This is my understanding of the feelings Woody experiences and the reasons for every single one of his actions.
................................................................................................................................................................................................................... Teaching how "to let go" to a child audience by separating two main characters and doing it WELL. In this case, Woody and Buzz instead of Ralph and Vanellope. While the latter insisted on a big no-no (CHARACTER REGRESSION), something you do NOT do unless you want to make your character into a villain, TS4 handles it subtly and intelligently because Pixar is more like that....um most of the time lol)
So, firstly we are shown that Woody and Bo were very heart-broken when they parted. "Why doesn't Woody show this attachment in the third movie?" you might be asking. While, yes, he was shown to be a little sad and then it's never spoken of again. But Woody was still very focused on "being Andy's best friend" and the leader of the others. So his life still had purpose. Bonnie found him and he did let go of Andy, PHYSICALLY, but it's hinted all throughout this entire film (4) that his emotional attachment to Andy is as strong as ever and he is subconsciously trying to replace Andy with Bonnie.
But Bonnie does not have the same attachment to Woody as Andy had to Woody; she is much younger and children are really fickle. This may sound sexist but I honestly feel it's true: "Girls bond tighter with toys of girls". I am speaking out of personal experience as a woman. Bonnie is revealed to be more attached to Jessie "because she's a girl like her". This isn't retconning Bonnie's fondness of Woody in the third movie, as you remember, he was the FIRST of Andy's toys to be introduced to her. Then Andy gives her Jessie later and she grew to prefer her over Woody. Woody is losing one of his purposes: "make Bonnie happy because that's what Andy trusted him to do" but he is also losing his position as "Leader" as well. Bonnie's room already had a flock of toys before he got there. Everyone seems to be fitting in great but he's an outsider. He longs for the past where he had everyone's trust and respect and Andy's affection. Along with this trip down memory lane, his feelings for Bo are resurfacing.
Then he sees that Bonnie is feeling sad and frightened at the idea of school and leaving her room. A toy's purpose, along with making a child happy is "to give them security" so he takes this to heart and comes along to make sure she's okay. Bonnie then creates Forkie, whom she grows obsessed with because "your first childhood creation is extremely dear to you" (artist perspective). In a way, it's your own child, something you've made with your own hands. Woody is delighted to be Forkie's baby-sitter, because as long as Bonnie has Forkie, she will be happy; thus Woody IS capable of making Bonnie happy, indirectly through Forkie. And he becomes completely OBSESSED with this new "purpose" because it is his only mission he has and he is clinging to it as tightly as he can. But it still feels hollow because he's still not getting the affection he longs for; so he's thinking about his old first love again.
After reuniting with her, even though she has changed, Bo Peep is still the one he loves (well it seems even more so now) He meets new toys and has adventures with them, (during which we are taught that he's taking his obsession of making Bonnie happy to a very bad level and he still feels "lost") yet he helps a toy (Gabby) connect with a child again; this reflects the situation from the first movie where he got Buzz to accept he was a toy to make Andy happy. Gabby was previously rejected by the child she longed for. This reflects Bonnie's absence of affection for Woody and Woody's eyes are opened to "Wow...I can be wrong sometimes?"
But Woody is loyal so he thinks he needs to return to Bonnie, even though that's not what he TRULY wants anymore; what he now wants to stay with the only woman he has ever loved and rescue lost toys and help them bond with children like he did with Gabby. We see that he and Bo are experiencing the exact same heartbreak from the beginning of the movie. Buzz however has known Woody so well that he can see right through him and convinces Woody to finally go after his OWN happiness in a tear-jerking farewell.