What combination of OS X, Endnote, Word just WORKS?

You definitely should not have all those duplicated entries. Here is what I would recommend:

  1. Start Word, go to “Word > Preferences” and click on “File Locations.”
  2. If the Startup folder is not set, highlight “Startup” and click on “Modify”. Select the folder Applications : Microsoft Office 2011 : Office : Startup : Word and click “Choose.”
  3. Click “OK” and close Word.

Now, do the following:

  1. Browse to the “Applications: EndNote X8: Cite While You Write” folder.
  2. Copy the file “EndNote CWYW Word 2011.bundle” by highlighting the file and going to “Edit > Copy.”
  3. Next, browse to the “Applications : Microsoft Office 2011 : Office : Startup : Word” folder.
  4. Delete all the EndNote files here.
  5. Paste the “EndNote CWYW Word 2011.bundle” file.
  6. Start Word.

There should now be 3 items for EndNote under Templates and Add-ins in Word:

EndNote Cwyw Commands.dotm (checked)

EndNote online Cwyw Commands.dotm (unchecked)

EndNote CWYW Word 2011.bundle (checked)

If you see any other files, remove them. When you click OK, see if the EndNote option is under the Tools menu and the toolbar is checked under the View menu > Toolbars.