How to use Chicago Manual of Style with superscript cite numbers and sequential endnotes instead of footnotes?

I will try to get you started.  I am not a humanities footnote guru though.  

I have Chicago 16th footnote as a style which includes both footnotes and a Bibliography.  

In Word you can insert your “endnotes” instead of inserting footnotes from the “References” tab.  You can adjust endnotes numbering to be 1,2,3 and they will be superscripted (mine were originally set a i , ii etc and I needed to change them to 1,2,3 numbering which I did by using “tell me how” box and just picked “endnotes” and the options popped up).  

Now, you may want to edit the EndNote**   specifics for each reference type in EndNote’s output style (save as to a new name- so you know it is the right one) to remove the final period, as you often want to introduce additional text after it – you can enter your citations into the endnote itself (not into the text).  and type the other text you want to appear.  I find this easier than to use EndNote’s “edit citation” tool to introduce prefix or suffix or cited pages information into the _endnotecitation _ introduced by Endnote.**  You will need then to manually enter the period too, where it belongs, and any additional punctuation, if you cite two citations in the same footnote, for example.  

so for example – I added 3 separate citations to an “endnote” (not 3 at once) and added some intervening text (I didn’ t remove the offending period from the templates though, if you did, you would need to add back a period where you wanted one to appear).  Doing it this way, I could also add the semi-colon space, where I wanted it to appear.   I am not entirely sure how to get the endnote number not superscripted though, in the “endnotes” section.  

The Chicago 16th footnote output style , gave me the text as shown in the image attached.  

One caveate you will notice is that the EndNote inserted Bibliography is appearing before the endnotes rather than after them.  I am not exactly sure how to override that.  Maybe a user more familiar with footnotes/endnotes and EndNote can comment? 

If it were me.  When the whole thing was ready to submit.  I would remove field codes or use Endnote tools to “convert to plain text” (ON A COPY) and move the EndNote generated Bibliography into a new document.  I don’t know how to get Word to allow text to be positioned at the end of the document after the “endnotes”. 

Hope that is helpful.  You may need to tweak the footnote templates in the output style further, or the bibliography templates.  Those are separate sections of the  EndNote “Chicago 16th footnote” output style for the reference type templates ( see second image ) for footnote (which also affect the output style’s handling of Word’s _endnotes)  - see third image _. 

EndNote’s footnote templates (in EndNote Chicago 16th footnote output style)  also have a long and a short form (first time cited and subsequent times cited) 

Now I tried to put Endnote things in bold and Word’s endnotes things in italics, but it is still probably as clear as mud!