This is all very helpful. It hadn't occurred to me for some reason that Delta wouldn't have their own direct flights from the NYC market. Connecting through ATL, DTW, or LAX would all be doable. I will call the DM desk and ask about upgrade inventory on flights through those cities on my preferred dates of travel. Assuming there is none right now and they won't be able to clear me at booking, should I wait a month or two and call again? Or should I pick a connecting city and book now (and if so, which one?) in order to get my request in ahead of other DM's with GUCs?