May not do entirely what you're looking for but you can change the wav file associated with various windows functions including windows start up and shut down.
Go to Control panel, open "Sounds and Audio Devices" click on the "Sounds" tab. There in the dialog box are all the sounds associated for each task, scroll down, you'll see windows exit before windows start up. There you can browse to other wav files to associate to the given task.
I don't think it will play multiple wav files, so you will have to make a wav file that has the gaps you need, to simulate the chain of events you want to audibly create.

Sounds like a fun project anyway,
hope this helps or gets you on the way

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