How to open a file the next time the Windows computer boots?
Open the Registry Editor, and add the filename as string to HKEY_CURRENT_USER\Software\Microsoft\Windows\CurrentVersion\RunOnce
when you are logged in as that specific user, or to HKEY_LOCAL_MACHINE\...
which opens that file for ány user.
Just leave him a post-it note... or two. Assuming you leave one note for each problem you fix... I assume you'll end up like this: