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.
Broken Base/They Changed It, Now It Sucks: Did the series break when A.) They started making material past the 1980s stuff. B.) They introduced villains and generally re-tooled the 2003 series. C.) Demoted Honey Pie Pony and the existing Fillies to extras, then immediately shove them on the bus, and then introduced new, bland Fillies with no personality in the formers' place a few months later. D.) Reboot the franchise again in 2009 and made the new show CGI. or E.) or did it never break?
Germans Love David Hasselhoff - It had and has a strong following in Mexico among both first-generation fans and girls who watch the remake, where it is called "Rosita Fresita". It may have even contributed to the slang "fresa" [strawberry] being synonymous with posh and over cute, or "Valley Girl.". It also has a berry, berry strong following in South and South East Asia, specifically in India, Malaysia, Singapore, Indonesia and The Philippines. Even to this day merchandise of the 2003 series (specifically, Baby Strawberry Shortcake products) are still being made and sold in the mentioned countries, in addition to 2009 reboot clothes(for older kids), stationery and body care products.
The 2009 series are starting to go moe again after they revised Strawberry to go without her (ridiculously dated) balloon hat in some of the newer merchandises.
Periphery Demographic - It's not just kids who watch the TV series and specials, and collect the toys. However, special mention go out to the early episodes of the 2003 continuity for not only attracting the adult collectors but Slice of Life fans as well.
Tastes Like Diabetes - One could say the 2003 reincarnation, up until the reintroduction of villains, was this. As is the 2009 franchise.
Coupled with Does This Remind You of Anything? for Plum Puddin' in the '80s. Plum is a boy in the first episodes. Plum is missing in the middle episodes. Plum returns to Strawberryland as a girl for the final episodes.
Almond Tea, although unlike Plum Puddin', she had always been a girl.
Also in the '80s, Souffle the Skunk is called by both male and female pronouns. Souffle's voice actress often played male characters, to further the confusion.
In the 2003 remake, possibly as a homage to the '80s Plum, Plum Puddin' is assigned to a horse who is referred to by male and female pronouns.
Genius Bonus - The Purple Pieman's competing recipe in the Big Apple City bake-off is one for "kohlrabi cookies" — kohlrabi is a variety of cabbage. No wonder the results are bad!
Paranoia Fuel and Adult Fear: The first special will get children to think twice when strangers come up to them and try to sell them anything. Not that it's a bad thing of course.
Recycled Premise - Strawberry's toy company Kenner swapped out fruit/food for flowers to create the characters and setting of the similar (and scented) toy line Rose-Petal Place in 1984, which spun off two animated specials.
What an Idiot: Arguably, Strawberry Shortcake's friends in the third special. Let's review the situation: Strawberry is prone to bursting into tears at the mere thought that someone might not like her or think badly of her. Also, most of her behavior is motivated by a desire to constantly make others smile and be happy, and she's perpetually friendly and loving. Meanwhile, the Peculiar Purple Pieman of Porcupine Peak previously attempted to flood the land and later attempt to cheat someone out of a gazebo, and every time he ever appears he's always up to no good. But when the Pieman claims that Strawberry helped him rig a pets on parade contest in his favor, Strawberry's friends jump to the conclusion that Strawberry's a cheater because THE PIEMAN SAID SO?!
The 2003 series
Accidental Innuendo: In the song I love Custard from the episode Here Comes Pupcake. The title of the song itself is a little cringe-worthy as-is, but the absolute gold has to be the line I could eatmyCustardwitha spoon, sung by Strawberry Shortcake.
Channel Hop - In Asia, the 2003 series actually moved to Boomerang after Hasbro took back the master rights of the franchise from Playmates Toys, due to Hasbro's meddling (Prior to this, the show aired on Playhouse Disney Asia, and before Playhouse Disney Asia was launched, Disney Asia as part of the Playhouse Disney slot). This actually resulted in tons of inconvenience and made the show unavailable to Malaysia and other countries that do not have access to Boomerang, since Season 4 was never released on home video in Malaysia (and it's probably safe to assume the same, if not the entire series, in other countries). Nice Job Breaking It, Hasbro!
In Legend of the Lost Treasure, the Sea Beast makes a heel face turn and narrowly escapes death. The adventure ends with a song about treasuring friends. A few months after said episode was made, the character's voice actress died. (The Sweet Dreams Movie was dedicated with love to Pam Carter's memory, as mentioned in the closing credits.)
The death of James Street ventures into this territory. His character, Huckleberry Pie, often used a skateboard to get around Strawberryland. Riding without a helmet, Street was in a fatal skateboarding crash. (Daniel Canfield voiced Huck for the remaining seasons.)
Painful Rhyme: "The right ingredients, the right ingredients! If you've got them, you'll make friends with super-speedients!"
The 2009 series
Mondegreen: Happened to some during the Berrykins' song in "Sky's the Limit!". The fast, pitch shifted voices singing sounded incoherent to some viewers, and resulted in strange lines like "Do we have a very nice butt?". It didn't help that the closed captioning was flashing by at too fast a rate to be comprehensible without pausing, either.