Strawberry Shortcake/WMG

Each remake features the same characters reincarnated, but given different identities and positions.
The exceptions to this are Strawberry Shortcake, Huckleberry Pie, and most of the pets.

The 2007 redesign is in an Alternate Universe of the 2003 series.
This theory is met with berry mixed opinions from fans.
 * Not possible, since the 2003 canon is retained in the 2007 redesign.

When the characters reach a certain age, they get the urge to hibernate
Probably eleven or twelve. They go into a month-long hibernation in mid-winter. Their body ages rapidly during the extended sleep.

Think about it: the episodes we've seen so far have early winter and near the end of winter, but nothing in between.

Before they hit that certain age, there is no urge to hibernate. They are simply trapped in their homes in the harsher months of winter.

In both the original series and the 2003 - 2010 series, Sour Grapes has a crush on Pieman.
So what if they are siblings in the remake?

Most (though not all) characters with purple themes have Asperger's Syndrome.
There are genetic factors involved, which means that Plum Pudding may be vulnerable to a Face Heel Turn (since evil is so often In the Blood).

Ditto Rainbow Sherbet, actually more of an Aspie than Plum, though Rainbow is also a stronger girl than Plum and would probably be the last to make a face heel turn.

In the original series, the title of Berry Princess is bestowed to a deserving girl upon said girl's reaching adulthood.
Strawberry Shortcake is next in line.

Pupcake is a lot smarter than he lets on.

 * This one's actually confirmed. The episode Toto's Tale is completely narrated by Pupcake.

Plum Puddin' is a male-to-female transsexual in the '80s
It's by magic, and it's still in progress.

The kids in the 2003 series are orphans, but most have had their painful memories erased.
Only Peppermint Fizz and Raspberry Torte can remember their old lives.

By 2007, Lemon Meringue was sick of following Raspberry Torte.
That is why she established herself as a leader.

The Sea Beast in "Legend of the Lost Treasure" died after reforming.

 * Prompted by the death of her voice actress, and...

In every series, there is some sort of curse that kills off reformed villains.
Yes, Redemption Equals Death is perhaps absolute. Hence, the villains are afraid of permanently reforming. Interpret the finale of the 2003/2007 series as you will.
 * Well, interpret the characters running towards the setting sun as the screen pans up and fades out (if Mayor For A Day is the actual final episode of the series).

The '80s Strawberryland is on the same exact planet and country, perhaps in the same exact state or province as Herself The Elf.
The creators didn't even try to make their worlds look different. The animation style in both specials is exactly the same from '83 - '85.

Continuing from the above, Creeping Ivy from Herself The Elf is the daughter of '80s Sour Grapes.
Since the two shows were created by the same people, this could easily have been intentional. Creeping Ivy is the splitting image of Grapes, sans the beauty mark, and Ivy was raised by her single father. Her personality is a mixture of Grapes and Thorn, to boot. The creators could have wanted fans to make the connection.