Unfortunately the only way I've found to prepopulate the initial start menu (what you see when you first click the start button) with specific shortcuts is to use a vbscript which invokes the "Pin to start menu (Classic Shell)" which works great, however when the script runs at logon, it keeps adding the same shortcuts to the list that is already there, creating a mess. In windows 7, the "Pin to start menu" function only worked for the shortcut if it wasn't already there. if the short cut was there already there, the pin to start menu function changed to "unpin from start menu". Then the vbscript to prepopulate the start menu never put up duplicates. It worked great.
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