Outspoken is not compatible with Classic, as far as I know.
That is my understanding as well. One must boot into OS 9 for OutSpoken to work. I understand your question now. You are asking if anyone has figured out a way around this limitation. I would guess not, if only because interest in Classic seems to be on the wane everywhere. On the other hand, if anyone does manage to get Classic to work on the Intel Macs, the same (virtualization) hack that allows that might well solve the current incompatibility between Classic and OutSpoken.
