To add more complexity to this decision, you want the BF on the outbound, not the return. IMO, if you could confirm BF out and coach return, I would answer differently than if presented with the situation you describe. Outbound is the night flight, and if you're going to tough that out in coach, the return is a piece of cake in Y.

Second, no reason to pay EasyPass for coach return when you can get BF confirmed. Isn't it the same price in miles? If you do decide to blow 75K miles on the ticket, get the BF return at least on that one for your daughter and split up. You'll earn brownie points for that. And you fly on the paid ticket and earn miles yourself.

Finally, I responded in your other thread to please be sure to check the other partners first (DL, NW, KL) as you seem to have originally been planning a coach trip. HOWEVER, that advice was given before I knew it was a $360 ticket! Pay the $360 each for both of you and earn 10,000 miles each for the trip. And that's presuming you have no status with CO. Book online at continental.com on separate records for another 1K each.

Save the miles for when the ticket would be more.