I think I figured out why I didn't get credit for my Move Streak in October. My Move goal is 700 kcal/day. I decided to restore my iPhone last Sunday morning and it caused my AW to repair to the newly installed iOS. OK, so I ended up with 750 on my Move for the day.
The only problem is that I had 75 kcal before I restored the iPhone, and 675 after. I think, even though, I broke 700 for the day and the Activity app on the iPhone shows 750, the achievements see 675, so I lost the streak (which was at 308 straight days) for October.
I'm hoping that it'll fix itself, but who knows.
For those of you that actively wear 2 different AW's, do you get acheivements if neither watch got the move goal individually?