To get a list of Recommended readings (not necessarily cited?), separate from the cited sources (as footnotes)? Is that what you are trying to get?
So Cite things in footnotes, and then -why not use a label or other custom field to put a specific “topic” in the records themselves, and then generate subject bibliographies using the “subject bibiography…” tool and paste them in the specific place in the text you want them to be. You might be able to do something similar using the groups of Endnote XI, but since I haven’t upgraded to that, I can’t suggest the best way to achieve what you are working toward. They will not be dynamic, but once you know what you want to list there, do you really care? You can later add another one (using the copy format) or generating a new list and replacing it. – I guess I am happy I am in the sciences and not the humanities!
With the subject route: This will generate a list or lists sorted by the selected subject which can be saved to a file. You can generate a document with several subjects listed separately, which you can copy and paste each section, into your document.
Again be sure the Endnote program has the appropriate style selected so that it outputs the information in the specific format you are looking for. It really doesn’t matter if it originates from the footnote syle or footnote/endnote style of Chicago. Copy and paste the template you want from Chicago into the bibliography place (of a copy of Chicago if you like) and use that saved new style to generate the copy formated to paste or the subject bibiography.