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That said, since you have all characters, I personally suggest playing them in the order of the non-antagonist vanilla characters (Filia, Cerebella, Peacock, Fortune, Parasoul, Painwheel - in any order), then the two vanilla antagonists (Valentine, then Double) and then the DLC character stories in order of release (Squigly -> Big Band -> Eliza -> Beowulf -> Robo-Fortune), since that's how everyone else went through them.
Oh and of course Fukua somewhere in there, though Fukua's story is mostly a non-canon joke/excuse to fight, so really just play through that when you feel like it.
They're technically the end tales (more-so Double's tale), but they don't really have any tie-ins to the actual story.
There seems to be no "cannon" Story in Skullgirls, and each Story has no real connection to each-other.
With that in mind, I'd highly suggest doing the Vanilla stories first. They have no (or at least very little) connection to other characters.
The DLC characters seem to always have at least one other Skullgirl (or major character, at the very least) intertwined with their plot.
Also an important thing to note is the DLC release order. The newer DLCs seem to take more references. Newer DLCs also have older DLC characters to fight against.
So at the end of the day I guess:
All starting non-DLC characters -> Valentine -> Squigly -> Big Band -> Fukkua I guess? -> Eliza -> Beowulf -> Double
The antagonists are fun to play last though. You can try doing Eliza's story (second) to last. It's quite the spectacle. More impressive than Double's, in my modest opinion.
Also if I had to order the vanilla characters: Cerebella ->
For the feelsy reasons.