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If the problem to solve is piping an emacs buffer to a Windows 95 text mode binary and replace the buffer with the text output, the solution could be
1. Run Windows 95 in an emulator, maybe a webassembly one.
2. Generate the mouse clicks and keyboard events to run that program, probably in a full screen DOS window. It must be in the %PATH%
3. In the same way type in the buffer in the input of the program.
4. OCR the output.
5. Replace the content of the buffer.
I think it is feasible.
Step 1 is for example https://github.com/felixrieseberg/windows95
I wouldn't be surprised that steps 2 to 4 are already implemented in some form.
Step 5 should be trivial.