B-Day set up in Address book shows up in iCal but won't sync to iPhone

And it would be my Mothers! I don't sync over air. Always sync through iTunes,, and I have marked "all iCalendars to sync".. I have 3 calendars plus a Birthday's one. I also have a "Birthdays Calendar". After I sync, all the Birthdays EXCEPT this particular one are there. My Birthdays are set up from my Address Book. I presume that is how most of my Birthdays got to appear in the Birthdays Calendar. I can't understand why this particular one doesn't show up. I have deleted the contact (my mother), and re-input, including birthday(obviously), but won't appear still after sync on my iPhone. I did try a separate entry into iCal, adding a Birthday event, and this time, that one showed up after Sync. Can anyone explain, why the separately added on into iCal showed up in my iPhone, and the birthday attached to my address contact in Address book didn't .. or is it a quirk (black hole event).

Let's see, uh, these are shows I downloaded 6 months ago, so I guess the answer is... no?  Not so simple?
I looked a lot closer and apparently the shows I bought before are just gone.  I went back to the store to repurchase only to be told I already bought them but if I want to I can buy them again.  Not redownload but actually repurchase.  So no, not so simple.
Something must have gotten corrupted and apparently once that happens then things get squirrly real fast.  That's ok, I have an engineering degree and am computer literate.  Imagine my mom trying to mess with this?  No way. 
So no - not nearly simple enough.

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