I've given up trying to educate people in how to use their computers without installing malware.
What you should do, apart from the innuhneh filtering, is get his computer clean and updated and working perfectly with all the software he needs installed on it, take an image of the boot HDD with Acronis TrueImage or similar, and install a second 'data-only' HDD and make sure he knows to store all his data on that one.
Then, whenever the mood takes you, you can dump the image back onto the boot disk, run Windows Update, and hand the machine back to him in the reasonable certainty that it is free of evil. Faffing about trying to surgically remove this week's spyware/rootkit/etc is for the birds.
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