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It’s pretty common to end up with cracked solder joints on those analog boards, especially on the connectors. I would try reflowing the solder for all three connectors on the analog board (deflection yoke, CRT neck board, logic board) and see if that fixes the issue.

Given that the IWM seems to be fine and that you’re experiencing the same behavior with the external 800k drive and Floppy Emu, it sounds like there must be a bad line somewhere between the IWM and the floppy port. Could be a problem with the line filters, or potentially bad/intermittent contact...

I’ve found Option+Command (M0110A keyboard) works on my Plus for sending Control within MacTerminal and some other terminal emulators.