Former Microsoft employee that worked on MyFordTouch for a little while.
> Rumor is Ford outsourced to Microsoft who outsourced to someone's cousin who wrote it in Adobe Air or something
That's actually pretty close. From what I understood Microsoft and Ford worked pretty closely on SYNC and that was a large success. Ford came back to Microsoft to have them do Sync 2.
Microsoft gave them a quote saying it would take $X and Y time. Ford said it needs to be cheaper and faster. Microsoft told Ford "We can't do that, here are some of our preferred contractors for Windows Embedded, maybe they can."
Some time later Ford came back to Microsoft saying "Please fix this" and that was around the time I joined. I actually heard a Ford VP say "This is the worst quality problem we've had in my time at Ford." He had been there during the Firestone tire debacle. (He was talking about cost in lost sales, obviously iPods not working wasn't as bad in the grand scheme of things as cars rolling over.)
The "backend" of the system was written in C++ on Windows Embedded. The user interface was written in Flash with some insane stringly-typed interface to talk back and forth with the C++ layer. And that's how I became an action script developer at Microsoft for a (very) brief time.
iPhones worked decently with the system. Android barely worked at all (Ford didn't care much about that at the time). Windows Phones actually worked pretty well since all the employees at the time had them and that's mostly what we'd use for developing.
It was the worst job I've ever had.