Why does he need to use Outlook? He uses Yahoo mail. He managed to install iTunes. The printer installed without a hitch via the HP software. Windows updates install themselves these days unless you disable it.

My mom is paranoid about viruses and installed Symantec, but the paranoia also ensures that they don't click on weird crap coming thru email. Sidenote: my mom upgraded the laptop herself from Vista to Win7 without bugging me, praise jeebus!

PCs aren't mystical, I don't know if the expertise of maintaining them is some kind of totem that geeks cling to but hearing about problems with them is the exception instead of the rule these days.