I would agree with you. In Princess Bride, which is almost entirely a flashback, if they'd segued off into a scene of how Westley became Dread Pirate Roberts, it would be fine - it's a storybook being read, and books often have out-of-nowhere asides.
If it's a character having a flashback, and then there's a flashback inside that... well, the only ways I can think of to pull that off would have their usefulness more in getting the reader/audience confused and off-balance than actually relaying information. I'm thinking Run Lola Run, with the flash-forwards. Amelie also does it(?) - flashing back to when she was a kid, and then moving around in that timeframe.
It'll probably come off disjointed, but that's a useful tool, right?
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