Some ideas are running through my mind. Why not make a US B stick with an autorun.inf on it. The only thing I need to do is to insert this stick at the moment that his desktop is unlocked. The only downside is that this does not work for USB sticks. This is only native supported for a CD.
Now I can do a couple of things. Insert a CD in his drive and not close it completely. At the moment that the desktop is unlocked, give a push to his cd drive and hope it spins up.
The second idea is to make a longer usb cable and attach a CDRom drive to his laptop. This CD drive can then be switched on by an automatic timer, giving it power.
The third idea is to buy a USB stick which acts as a CDRom drive. I know these devices exist somewhere.
I will let you know . .. I want to get the keyboard logger working first.