When a User preference is applied it is applied in the context of the username, so you will get the user's environment variables. To clean files from the user's start menu, do the same thing under your User policy.

Group Policy Preferences are executed with privliged credentials folder deletes will happen when Group Policy is applied.

If you are hunting for specific files that are mixed in with other files that you don't want to delete, put those files in Computer Configuration > Preferences > Files. Whatever actions you specify here will happen on every computer the policy applies to, but because you are doing this on the computer level it's best to stick to files and folders that are present on every computer. Under Computer Configuration > Preferences > Folders you can create/delete folders. Open up the Group Policy Management Console and edit the policy applied to your computers or create a new policy. (For Group Policy Preferences to work computers must be joined to Active Directory, users must be logging in with Active Directory accounts, you need a Windows Vista or higher computer to configure Group Policy Preferences, and Windows XP needs a specific update available though Windows Update installed to run Group Policy Preferences.) You could script the entire operation and spend a few hours testing and verifying the script before setting it loose on your users and their computers, or you could spend a few minutes in Group Policy Preferences to accomplish the same task.

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