Here's an updated spreadsheet/calendar.  I think this is the correct logic.  Just don't know how to make it work (unless you know the Cross Apply thing will work for this)

Thank you Drew.  I think I follow what your saying and asking and the possible issues/flaws in my logic.

I'm attaching a more detailed file that explains the daily...

Drew,
I ultimately ended up with the following for the CASE statement part:

AND