Ahsoka: CW - The battle above Ryloth. She would listen to orders this time and not get a bunch of clones killed. Rebels - Hmmmm Part of me wants to say to do something to have saved Anakin, but she admits that is not her place. Maybe to have known about the controlling chip in the clones earlier so she could save more of her brothers?
Ben - Whatever got him killed.
Dog - I can't help thinking she'd like to have stood up for her obnoxious brother more back when he got punished for not helping them with the other asshole brother, but I have no canon source for this. And to be honest, I doubt it would have changed anything.
Emcee - Had he known how difficult everyday life was going to get, he would have left Germany sooner.
Cassidy - He wishes he hadn't been such a coward. Instead, he watched his best friend die and ran away. Which led to him hiding in a swamp, which led to him being bitten by a bog hag. So if he'd just tried to save his friend, he would never have become a vampire.
Yamato would go back and take more steps to avoid the deaths of Gabumon and the other partner Digimon, now that he has the benefit of knowing that they were dying.
At the top of Amascut's coulda-woulda-shoulda list is a bunch of regret that she didn't fight harder and teach her followers more about demon and vampire slaying in the early decades of the Zarosian/Demonic incursion. There were unspoken rules that prevented divine intervention that might escalate to pivine warfare and god slaying, but she could have done more. And the worst of it, a god slaying happened anyway followed by a millennia long god war, partially due to choices that her brother made to defend against the Zarosians and the quest to find defenders that stranded her on the other side of the universe. Oh, and her father sorta died when he nuked the subcontinent to defend it against the Zarosians too. Sorta.
She regrets how much she did teach her followers after she found her way back home and before they betrayed her, though. So, fixing her past mistakes is a fantasy she avoids because she can't think of good outcome.
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*eyes the end of season 1*
...
*eyes the end of season 2 and how it turns out in the start of season 3*
*SOBS*
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Rebels - Hmmmm Part of me wants to say to do something to have saved Anakin, but she admits that is not her place. Maybe to have known about the controlling chip in the clones earlier so she could save more of her brothers?
Ben - Whatever got him killed.
Dog - I can't help thinking she'd like to have stood up for her obnoxious brother more back when he got punished for not helping them with the other asshole brother, but I have no canon source for this. And to be honest, I doubt it would have changed anything.
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Cassidy - He wishes he hadn't been such a coward. Instead, he watched his best friend die and ran away. Which led to him hiding in a swamp, which led to him being bitten by a bog hag. So if he'd just tried to save his friend, he would never have become a vampire.
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...
Yeeeah.
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She regrets how much she did teach her followers after she found her way back home and before they betrayed her, though. So, fixing her past mistakes is a fantasy she avoids because she can't think of good outcome.
She still teaches, though.