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Normally I would, but since this is messed up with their ages and stuff, I wouldn't think they would apply. Normally I would say Fluttershy's parents kicked her out after she got her cutie mark, and Rainbow Dash lived with her uncle and aunt, or at an orphanage since she's not all too good at school. I'm a depressing person aren't I? XD
I'll be Rainbow Dash then. I still think that Fluttershy should be older, though maybe only by a few months. Just seems right to have Dashie as the younger of the two.
I'm doing several adventure ones, which is why I suggested slice of life XD And true, though it would make it more fun for them to shift the ages around. Who would you like to play?
I'm partial to slice of life. I mean, they could end up back in diapers and after a few weeks try to start toilet training to no avail. Then we could easily skip forward to their first day of school, in which they are both still in diapers. Since Fluttershy is older than Rainbow Dash, she could start school late to be with Rainbow Dash so they aren't separated.
I'd say starting Fluttershy off in training pants, but then she'd be put back in diapers because well what you said. I think there could be certain elements of mental regression, like tendencies to be distracted by simpler things and the like. Nothing too major, just enough to where they're slowly coming to terms with wearing diapers. And since they're young, they wouldn't be able to leave Cloudsdale for quite some time. And I think the change should cause them unable to to start toilet training at a proper age. Just to make things more difficult.