I always eat in the lounge where possible, IMHO the food is better than on board plus you'll get more sleep on a short East Coast flight.

Re breakfast I always find it ok on the plane though my aspirations don't go further than a bacon roll and a bowl of fruit. The arrivals lounge is better I think so I normally sleep on board if possible but 9/10 times breakfast service wakes me and I eat on board without any reservations.

Difference between NF and CW is bigger now I think. I got to try NF out of JFK in Nov so think your chances are pretty good on that route. I'm not sure I'd pay £300 for a short flight where you're going to sleep though, especially given that you've got a good UD seat. I would only do that if you wanted to try NF. The CCR at JFK isn't that special, though it's nice and quiet.

Hope that helps.