The issue you may have is that since the OS 9 System Folder was not on the Tiger partition when you installed it, parts that are needed for Classic were not updated within it. I can always send you my email 10.4-based OS 9 System Folder and see if that works.
Also, unless you are doing two...
Thank you, but can you also show me how to strip all of that out?
As far as files, I regularly use macOS 10.14, and 15 and save files on a CF for my 1400...no issue.
I'd probably think a filter issue, there can be ghosting issues if they are not working properly. Best thing to do is to test the filters (basically a resistor pack) against states values in the Pina guides:
https://vintageapple.org/macbooks/pdf/Macintosh_Repair_&_Upgrade_Secrets_1990.pdf
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