Thank goodness for other people's ability to cap episodes...according to
this post by
muridae_x Free to Be You and Me takes place during the week of August 23rd. I'm not sure how that meshes with the Captions...but that would indicate that Sam and Dean actually spend 3 months apart, and Fallen Idol actually brought them into September, rather than my original calculation of July.
Interesting...part of me really wants to timeline this season as it happens...because sometimes dates on laptops (or x-rays, as the linked post points out) can just be flat wrong.
Hmm...