I'd probably go ahead and book flight 1, that doesn't sound too bad.
For flight 2 I'd setup a fare alert and see if you can get a not horrible rate. Really for Christmas/NY the more flexible you can be the better.
Ditto this. I use Yapta for fare alerts. Also I've found that fares really are cheapest when you book on Tuesday/Wednesday, particularly compared to weekends.
Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one's lifetime. Mark Twain