I doubt anyone cares or even remembers, but I thought I'd report back for posterity's sake. (http://xkcd.com/979/)

I was able to use CO miles to book 3 of us (not including the baby) on TK: BOS-YYZ-IST-ISB (first leg on AC). Using continental.com, the booking process was very easy, but they screwed up on the infant ticket so I had to call in anyway. The infant ticket was much more expensive than I thought it should be, but I'm still pretty satisfied overall.

For the return, I adjusted my plans a little and am now stopping in Saudi for a couple days. I used AA miles to book myself JED-AUH-ORD-BOS on Etihad (last leg on AA) in J. I went with business class mainly for the experience, hopefully I don't get spoiled. Booking the ticket on the phone was easy, but I did some thorough research before hand. Had to pay the phone booking fee even though there is no other way to book. I'm pretty excited for this flight, even though it's longer than necessary.