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Terrible hardware life-cycles and zero support/poor treatment of third-party developers.
Poor timing also played a huge part of why they're not a player nowadays.
That said, the Dreamcast is one of my favourite consoles ever made. Such a shame.
Sounds like a corrupted backup. Try syncing only your contacts/mail to iCloud, then run a fresh restore. Once it's up and running, sync your details that you saved to iCloud.
I've gone back to my original character now because the second one (Lv76) made things too easy. lol.
It's much more satisfying playing it on the hardest setting too. You can't simply slash your way through everything.