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Edit: For now, you can try the flycast from the repository and see if it's any diferent. Not sure you can get Retroarch achievements that way though. Or if you have Retroarch Standalone with "Flycast" and "Retro Dream" cores. The latter is discontinued but might still be found with a google search.
My first thought often goes straight to "it's a bios issue." In your RetroArch/system folder, is there a folder labeled 'dc' with your legal bios placed within?
It is also possible that your .cdi file is just borked. This file format was initially used to compress DC games to the size of a cd-rom, so it isn't the best format to use.
Try a game in a bin/cue or a gdi format - those are the two formats that would work best.