Applied synchronicity

I'm relishing the brilliance of Bob and Ray, listening to a collection of mp3's: 5 days and 22 hours of them.

They should be indexed, I don't have 6 days to devote to the project.

How could I multitask, do the indexing efficiently in the background?

It seems it could be done via time-based data matching. The audio player logs timestamps with filename as it plays the set of files. I record voice messages describing what skit is being played, these voice files are timestamped. An application matches words in my voice recording with the index into the file being played.

The ideal would be a wearing a bluetooth mic, speak into it to record an index into the currently playing file.

A more accessible start towards that goal would be to provide the index info via keyboard instead of voice.