On this subject the git-annex website seems to be in error at present. I note that, according to the website, you should be able to call git annex sync --content --all to have git-annex consider all files, including unused files, as it computes the files to transfer according to your...
I do not believe that you can do this with git-annex as it stands, based on my reading of the MATCHING OPTIONS in the git-annex man page. Note that there are no options that consider age. Therefore, I guess that you would have to write a script to use git...