It's far more acceptable to modern sensibilities than the 1962 annual, but its innocence creates unintentional amusement.
The page count's the same, but with only four (slightly longer) stories this time.
1. RUPERT AND THE OUTLAWS
Rupert gets involved with exotic and slightly gypsy-like outlaws. They dress him as one of them, which is amusing. (The outfit they give him is red, blue, green, yellow, purple, orange, black and white.) Rupert helps find a missing child with the help of a dog.
I like the ending. The outlaws are serious about not wanting to be found, so they lead Rupert back blindfolded and then leave him to explain to his friends and family why he looks like a Mexican bandit.
I also noticed that those blocks of prose at the bottom of the page are capable of being a little indigestible. They don't have internal paragraph breaks, not even for dialogue from multiple characters. Also, there are times when you'd miss important story information if you weren't also looking at the pictures and the rhyming couplets. You've got to read the whole thing.
POLITICALLY INCORRECT CONTENT: "The Chief moves forward, then he asks, 'Why aren't the women at their tasks?'"
2. RUPERT AND THE BLUNDERPUSS
I quite enjoyed this one. There's a cat with wings, summoned by the Chinese Conjurer when one of his spells went wrong. Hence "blunderpuss". Tigerlily appears. Rupert turning the tables on his sceptical Uncle Bruno is amusing.
POLITICALLY INCORRECT CONTENT: bwahahahaha.
I didn't mind the "velly solly" dialogue this time. Tigerlily's stopped saying "um" like Little Plum, so (unlike the 1962 annual) I think she sounds Chinese. It's still very broad, yes, but there's accuracy in details like R/L and TH sounds, verb non-declension and the fact that direct object pronouns are the same as subject pronouns.
The unintentional innuendo, though, is so prominent that for me the story's subtext overpowered its text. "Queer" is one of Rupert's favourite words and the word "pussy" also appears a lot here. Here's a more-accurate-than-you'd-think plot summary:
Rupert's having another of his queer adventures when Tigerlily demonstrates that in fact he's been chasing pussy. All his friends hate pussy. "How horrid it looks! Where did you get that ugly thing?" They all keep calling it ugly, but Rupert's been told by the Chinese Conjurer that getting pussy means always calling it beautiful. You must keep telling it how nice it is, even if you don't really think so! "Nice pussy," says Rupert. "Pretty pussy." Still not feeling very brave, he talks soothingly and realises that its fur is silky smooth if you stroke it.
When Rupert Bear sees Podgy come, he tries to hurry past his chum! Rupert holds the pussy tight to stop it from going for anyone else. Bill, Algy and Podgy watch in astonishment. "How on Earth does Rupert control that thing?" whispers Algy.
Rupert passes Uncle Bruno, who'd earlier gone into shock on glimpsing the pussy. "Uncle doesn't need a doctor," explains Rupert. "He isn't ill at all. He really did see that thing on the window sill. Look, here it is. Isn't it lovely?"
Gasps Uncle, "Well, I must confess, I cannot see its loveliness!"
The pussy climbs on a cottage's roof, so Rupert has trouble getting the pussy from the thatch.
Finally, the Conjurer explains that pussy shouldn't be running around for everyone to see, but instead belongs in Mystery-land. Tigerlily also loves seeing pussy and calls it beautiful. "Well, it's been a queer adventure," thinks Rupert.
(Alfred Bestall never married, incidentally.)
3. RUPERT AND THE PAPER-FALL
Predictable, if your head's in Rupert-space. It's Christmas and Rupert finds lots of papers with lists of names! Might all his friends be about to tell him they didn't receive their presents? Theoretically, the story's good and mental... but in practice the reader's always about ten pages ahead of it.
POLITICALLY INCORRECT CONTENT: "I wonder if those queer little men would know?" Also, Nutwood's neighbouring villages include Pussyville and Little Winking.
4. RUPERT AND THE SKY-BOAT
The most deranged and hence the best of this year's stories. Rupert meets an inventor and his machine for extracting sky-metal from the "upper air". (This means he's been sucking clouds from the sky and pumping them out in the local countryside.) Unless you hold it down, sky-metal shoots back up into the sky. We've invented anti-gravity.
Furthermore, this inventor has built an anti-gravity boat that's too small for him to sit in, but perfect for Rupert and his pal Margot! (Margot's a girl, so she's human. In Rupert's universe, male children are animals and female children are human. This isn't an infallible rule, but it's pretty reliable.)
POLITICALLY INCORRECT CONTENT: none.
The 1970 and 1971 annuals are rare, incidentally, although they've both since had Express facsimile reprints.
Overall, it's okay. I wouldn't call myself a Rupert fan, but I'm fond of him and I have childhood memories of enjoying these books. At worst, it's a bit rambling and you're unsure what the point is. Its weirdness can be inspired, though, and it has charm.