After reading through this entire thread and the associated links, here are things that nag at me:
— The Dunhams are said to have disliked Barry Sr. There is a quote from Madelyn that he was “strange.” In addition, unconventional as they may have been, they lived in a time when a pregnancy out of wedlock was shameful, as was interracial dating and marriage.
I don’t believe for one minute that they allowed Stanley Ann to live at home while she was pregnant and subject them to disgrace, unless they locked her up. And she doesn’t seem the type who would be hidden willingly. They shipped her — figuratively or literally — off somewhere, and that precludes a Hawaiian birth. Canada? Kenya? How?
— That hasty family departure from Washington State in summer 1960. It makes no sense. There would be a lot of clues to unanswered questions if we could only find out WHY they left Washington so suddenly. They ditched good jobs, a stable neighborhood, Stanley Ann’s plans for U of W, probably friends and neighbors — for what? A new home halfway around the world where they knew no one and the cost of living was higher and they took lower-paying jobs? Doesn’t pass the smell test.
Was one of the Stanleys in trouble? Would Seattle court records from that summer give clues? Was Stanley Ann already pregnant? Is there a FReeper in Chicago who might know Madelyn’s brother?
Do we have anything but 0’s word that he was born on Aug. 4, 1961?
— Does anyone have wills or probate records for Barry Sr., Stanley Armor Dunham, Madelyn Dunham, Stanley Ann Soetoro, Lolo Soetoro?
Thinking about Young Adult (YA) literature of even ten years later (Blossom Elfman's The Girls of Huntington House, 1972) I would imagine she'd have been sent to a home for unwed mothers. I'm trying to think about how the culture of that time was, and this would seem to be very likely.