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.
One (probably joking) interpretation of Owl from the 2011 movie paints him as the movie's Big Bad, suggesting that he knew perfectly well that he had Eeyore's tail, and that rather than come clean, he made up the rumor of a monster called the Backson in order to cover his tracks. It's still agreed that he's not as nearly malicious as other Disney Villains, though.
Angst? What Angst?: Sort of, Tigger does have the occasional bout of depression or disillusion, but usually he's pretty hard to get down.
Common Knowledge: Everyone knows that Pooh and friends live in the Hundred Acre Wood — except that they don't. "The Hundred Acre Woods" is actually just a small section of a much larger, nameless forest (based on and clearly meant to be Ashdown Forest in Sussex, but in the books just called "the Forest"). The only character who actually lived in the Hundred Acre Wood is Owl; the rest of them live in other parts of the Forest. Though this misconception is probably another result of Adaptation Displacement: in the Disney version, "The Hundred Acre Wood" is the name for the entire Forest.
Time Marches On: In the very first story, Christopher Robin accompanies Pooh to a tall tree so that Pooh can use a balloon to fly up to the honeycomb. Christopher Robin brings along his gun just in case. He later uses it in an effort to get Pooh down by shooting the balloon, but misses and shoots Pooh Bear himself! And this is played for laughs!
For this reason many adaptations illustrate this as a popgun.
Viewer Gender Confusion: It's not unusual for those not very familiar with the Pooh series to assume that Rabbit and Piglet are both female. Heck, it's not unusual even for those who are rabid fans of the series to sometimes still find themselves thinking this way, even though they know better. From the Viewer Gender Confusion page: "One is a nagging, Super OCD neurotic with a thing for doilies, while the other is a timid, high-voiced submissive wearing what appears to be a pink one-piece swimsuit. Even Roo's cheeriness makes him come off as more of a tomboy. Since the characters are mostly asexual or pre-pubescent, the Smurfette Principle isn't so glaringly obvious.
Lots of viewers are confused by Rabbit's personality and home decor as to whether he's an old lady or a gay man. (Or just British)
Also, Owl was depicted as female in the Russian translation by Boris Zakhoder and in the Soviet Vinni Pukh cartoons based on it (because the Russian word for "owl" is feminine), as well as in the original Norwegian translation of the books.
A special mention goes to The Book of Pooh because of "Do the Roo." In this story, Roo searches for his own special dance. Piglet recommends ballet and he dresses up in a pink tutu to dance it, and gets Roo to dress up in one too.
Well, masculine pronouns are technically used in the books, but a character whose gender is not an important part of the story (i.e. Kanga as a maternal figure) always seemed to have no gender.
Dorothy Parker: It is that word "hunny", my darlings, that marks the first place in The House at Pooh Corner at which Tonstant Weader Fwowed up.
Viewer Gender Confusion: Christopher Robin's rather feminine shoes and outfit (in the books) tend to confuse some children.
What Do You Mean, It's Not Didactic?: Although the tone of the original stories and poems is mostly tongue-in-cheek, many texts and books have been written that analyze and explore the deeper aspects of the stories or use the setting and characters to illustrate complex philosophical ideas. Perhaps most famous are Benjamin Hoff's The Tao of Pooh and The Te of Piglet, which use the characters to explore and explain various Taoistic principles. It works surprisingly well.
Base Breaker: A lot of book purists detest Gopher (partly for not being in the original book and partly for his early Replacement Scrappy status for Piglet), but he has a lot of fans as well.
Like Gopher before him, Lumpy has his fans and his haters. A lot of fans find him endearing and entertaining, while others dislike him for having turned the Heffalumps into cute and cuddly creatures instead of the unknown menaces from the earlier days of the franchise.
The 2011 movie. Some thought it captured the spirit of the original shorts well and others thought it changed too much (giving Christopher Robin a British accent even though he's supposed to be British, making the characters too 'modern' in their attitudes, etc.).
Ear Worm: Virtually any song, especially the series' iconic theme song.
She's also cast in something of a Team Mom role, mind.
There's also Darby from My Friends Tigger and Pooh.
This is averted, as Lottie, while having more experience of the outside world, is just as much a Cloudcuckoolander as the rest of the cast.
Ho Yay: Eeyore and Tigger share a few moments. note (Though, really, it seems to be more that Tigger is so love with himself that remaking Eeyore into his image is more a form of praising and worshipping himself. Note that Eeyore is able to foil this by pointing out that another Tigger's existence would make Tigger no longer unique.)
Hype Backlash: Minor one. The trailer for the 2011 movie made it look like the film would have the stories hit a kind of Cerebus Syndrome and become really deep and bittersweet. Well... it turns out it's even more comedic and bouncy than any of its predecessors! And it's only an hour long, with some people saying they now needed to wait four more years for an actual hand-drawn Disney feature instead of two!
"Ever have one of those days where you just can't win?"
Periphery Demographic: This is probably one of the few for which most people will unashamedly admit to being a member. Let's face it, most of Disney's Pooh releases are squarely aimed at preschool or early grade-school audiences, but if you ask most fans, they'll probably unashamedly admit to liking Pooh. And there are certainly merchandise releases out there for adults related to this series.
John Lassetter has said that the target audience of the 2011 film "transcends generations."
Replacement Scrappy: Gopher was originally intended to be used in place of Piglet in the adaptations to give more American appeal. Fans of the novels were against it and thus Piglet was adapted into "A Blustery Day" onwards, arguably allowing Gopher to be a fan favourite in his own right.
Ironically enough, there are several fans who view Lumpy as this for Gopher. Others view him as this for the (decidedly less cute) Heffalumps that were occasionally seen in The New Adventures of Winnie the Pooh.
Darby is a Replacement Scrappy to Christopher Robin in My Friends Tigger and Pooh. Although he has made an occasional appearance in the show, Darby has mostly taken over his role... which has not made her popular among fans.
Win Back the Crowd: The 2011 tried this for traditionally animated Disney. Whether or not it worked is unclear.
The Woobie: Nearly every blasted character has at least one moment as this. Piglet was essentially conceived for this role, however.
My Friends Tigger and Pooh
Foe Yay: Tigger admits to being able to see inside Rabbit's kitchen from his house in one episode. Rabbit isn't exactly pleased to hear this.
Rabbit: I have better things to do! Gardening! Cleaning! And putting up curtains so Tigger can't see into my kitchen anymore! *Storms away* Piglet: I think Rabbit's a little cross...
Tigger also calls Rabbit "Ra-Ra" several times during the series.
In one episode, Tigger goes to Rabbit's house to hear through the door, "WE'RE THROUGH!"
Rabbit: I never want to see you or your stripes again! Tigger: What did I do?
Turned Up to Eleven in Tigger & Pooh and a Musical Too. When Rabbit is declared mayor of the Hundred Acre Wood, he decides to limit Tigger's bouncing to 30 minutes a day and forces him to wear special anti-bouncing shoes the remainder of the time. The depressed Tigger takes to following Rabbit around the Wood, dogging his every step.
Rabbit: Tigger, why do you keep following me around? Tigger: Well, what else am I supposed to do? Rabbit: Something! Anything! B-but you can't follow me around all day! (Tigger continues to follow him.) Tigger! Tigger: What?
The Comic Strip
Crosses the Line Twice: In some strips, Pooh takes act of being an asshole to new levels, especially when he's being a douchebag to Eeyore.
The Woobie: Eeyore, this time being more open about his thoughts and having to deal with Jerkass Pooh.