How to cite unpublished letters from archives in Chicago 16th style?

We will need to know what fields all that info (generic) lives in in the record you created and the currently defined Reference Type for that record (Manuscript?).  

Try adding a comma after the author field if it is entered as 

Allan Holland to Stella Holland

should fix any author issues. 

If there is no title field, this would explain the empty “” as Manuscript is using the generic footnote template which is 

Author, “Title,”| in Secondary Title|, ed. Secondary Author|, Tertiary Title| (|Place Published|: Publisher, Year|; reprint, Reprint Edition|)|, Cited Pages|.

I would create a template for manuscript if you don’t use it for anything else. you might start with a template from one of the other reference types and edit it to retain the fields and  add additional fields you use, and reorder them as necessary.