This is only effecting 1 user out of 5 and the other 4 aren't having any issues and all 5 machines are configured the same.
If the above steps still do not work, you can delete the "Send to Net Documents" folder and then restart Outlook (make sure there are no email messages left in this folder tree before you delete it).
The folder will automatically be re-created after restarting Outlook.
They can view the contents using the File, Open, Other users folder command.
Sharing subfolders requires a bit more effort as the subfolders are not accessible from the Open Other Users Folder dialog.
Is the calendar connection opened “on access” or is the connection made everytime the user opens Outlook ?
What if the Outlook (2010, 2013) user has checked the “download Shared folders” to cache all Shared folders locally ?
In Outlook 2013, click When someone shares a folder with you, you must manually that person's mailbox to your list of email folders in Outlook 2013.
Any folders they've shared with you will be visible when you view their mailbox (all other items in their mailbox will not display).
Important: Beginning March 1st, 2017, Office 2013 will no longer be available for installation from the Office 365.
Please see the following document for further details: Office 365 - Microsoft Office 2013 path to retirement.
Are all calendars downloaded as the user opens Outlook ?