A logon script might be the easiest way. But, the trick with most of those things will be to get the script running not as an admin, but as the user. That way the script will have access to the users' data. Running as a scheduled task should be fine, provided you can give the task the needed permissions. There's no need to have the script in System32, though – that's a protected folder and Windows is a little sensitive about it. I wouldn't describe what you're doing as a "security risk" per se; I just think the tricky part is going to be getting the script "logged in" as the current user, so it can access that user's data. Login scripts run under the user context, so that might be an easier way.
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