Nice review, pretty much spot on with both pros and cons. Winnie The Pooh is about the one franchise Disney actually makes better with constant follow ups and spin offs, largely because they know how to stay true to or even develop the characters and universe. Only big complaint is, as said Eeyore feels like comic relief and about the one character that doesn't get deconstructed. Being Eeyore this admitedly would be difficult to pull off, but would have lots of potential.
Aside from the Blusterday Day short and the entire New Adventures series, this has always been my absolute favorite installment in the Pooh franchise. You nailed why it's also probably the deepest, too.
One thing I loved about this film is the twist that everything that made this a "grand adventure" (Scary rock, thorn forest, a deep gorge, Skull, the Skulasaurus) was actually all products of the characters' collective imaginations because the way Owl built up the quest scared them so much. You'd think such a thing would come off as an Ass Pull but it's actually really clever and makes sense.
This was one of my first Winnie the Pooh movies and I still love it. This is about as close as you can get to Darker and Edgier with a series as innocent as Winnie the Pooh and do it right. The story is quite sad at times, especially at Despair Event Horizon parts, but then it pulls you back with some really nice heartwarming/tearjerker moments reminding the characters and the audience that the friendships the characters have aren't going to break no matter what and how each character is so much more than they think they are.
I'm sure it's no coincidence that the darkest Pooh movie is also the most meaningful one. Pooh and friends do not get the Disney standard of suddenly discovering some inner strength that sweeps them to victory. They have to come to terms with their own failings - arrogance, fear, overconfidence - with no magical trinket or mighty hero to bail them out as things reach their grimmest.
The movie makes a point of reminding us that a lot of what looks so frightening is us frightening ourselves, right from the start with the mass panic over Christopher Robin's note that an observant child might notice doesn't say what they THINK it says at all. And it finishes with the spooky shapes shown to be just the character's imagination in the daylight on the triumphal march home. There was never anything to be afraid of at all! (If this sounds familiar, it should. It's exactly what your parents told you if you were afraid of the dark as a child! Sheer brilliance.)
The finale is a bittersweet, heartstring-puller between two best friends that doesn't promise "together forever" because that's not how life works...and Christopher Robin knows it if he can't bear to say it outright. (pun not intended) The coming of twilight at the end of the film is a subtle suggestion that something is about to end and there's no stopping it even as Pooh gets a simple, powerful affirmation from his lifelong friend. But it will put a touch of honey on the ending if you imagine the closing song sung by Pooh to himself the next day, when his best friend doesn't show up like he's used to. Because now the "silly old bear" knows he's braver than he believed, stronger than he seemed, and smarter than he thought.
"True friends are like a solid anchor; the links to either one will crumble from time or trouble but the part which holds firm will do so until the end of time." —- Anonymous sailor.
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one of the best non-cannon Disney films
The film is criminally overlooked. People shy away from it because it's a Disney direct-to-video sequel, but in reality it's one of the best Disney films.
Don't get me wrong, it's not perfect. Some of the songs are bland, and the butterfly scene was pure Filler, but... The song Forever and Ever captures the childhood belief that everything will always be the way they are now: that Christopher will always be a child exploring the Hundred Acre Wood and Pooh will never slowly descend amongst tons of garbage into an incinerator. Later on, the song Wherever You Are is the exact opposite of this: it's Pooh coming to the realization that he has failed in finding his friend, that he has lost someone without any hope of ever seeing them again, and that nothing lasts forever.
Also, the characters. At the beginning, the characters have individual strengths as established in previous films. Tigger is confident in his strength, Rabbit in his intelligence, Piglet in his ability to (eventually) face his fears when his friends need him, and Pooh in his faith in Christopher Robin. Over the course of the movie, every single one of them comes to the realization that they ARE NOT SPECIAL. Tigger realizes he is not strong enough to succeed, and briefly displays the worryingly suicidal trait of being okay with plummeting down a gorge. Rabbit realizes that he is not intelligent enough, and the gang is subsequently hopelessly lost because of it. Piglet realizes he cannot overcome his fear, even to save his friends. And Pooh realizes that, no matter how hard he wishes, no matter how hard he tries, he can lose a friend. Permanently. HOW MANY CHILDREN'S MOVIES DO THAT! When you need EEYORE as comic relief, you know shit happened.
Then they all get better. (Without Deus Ex Machina.) The characters are picked apart and then put together again, better than they were before.
This was this troper's favorite movie growing up, and objectively remains so to this day, without Nostalgia Goggles. Much like Toy Story, it explores the idea that children grow up and leave their toys behind, but until then they can have many adventures together in the Hundred Acre Wood. Give it a watch!