DVC reservation always first. We fly SWA and they are never have bookings that early and we book our room exactly at the 11 month mark. We can always get a flight from somewhere but will not get our resort if we wait too long.
We invariably fly Southwest from Chicago. We live closer to Midway Airport, Southwest 's hub, rates are always decent, bags do not cost extra, Midway is the nicer airport, and O'Hare sucks as an airport including being awful for on time departures. Southwest never releases its rates until 6 months or less before a time. Result: DVC always gets booked first.
Currently, I am in the process of planning a short trip, 5 days and 4 nights, at the end of August. Given the slim studio availability, my air reservation will follow my DVC reservation.
If you're going with the legacy carriers (eg. United, Delta), especially for certain times of year, it can be more cost effective to book 14+ months out.
The legacy carriers only allow you to book 330 days out this has been the case for a very long time (I was a travel agent back in the late 1980's - mid 1990's) so less then 11 months out. It actually works well with the 11 month DVC booking window.
We use either Jet Blue or SW since they have direct non-stop flights in our area. Last NYE time frame I ended up booking our flight home on Jet Blue since there fares were out about 1 - 2 months before SW and there rates going home were 120.00 one way but there flights to MCO were 335.00 one way so we took the chance and waited to see what SW offered - we were glad we did got SW for 180.00 One way when fares 1st came out. Once I book DVC I keep my eyes peeled for air.
We always fly Southwest, so there's not a choice about waiting to check fares. I book DVC at 11 months, and then wait to see what our airfare is going to cost us when Southwest publishes for that month. We haven't had to change dates, yet, because of airfares being too high on a given date.
I'm usually online with Southwest as soon as fares are announced, so we've always been able to get the web-only wanna get away rates.
Sometimes we spot a really good airfare and book it before it goes away. Then we scramble for a place to stay. We're not too particular about which DVC resort we stay at (but yes, we do Love OKW) so we seldom have a problem getting a room. We are also not above staying at a non-Disney hotel like the Swolphin if need be.
Other times we are planning for a particular event (like Festival of the Masters in November) and book our resort first based on the days we hope to be there. Then we start checking airfares. If there's a big price difference we will move our dates either way to take advantage of them. We also are willing to fly out of two different airports (BOS and PVD) and into two different airports (MCO and TPA) when we do this so our options are usually pretty good.
Around the same time, usually I book DVC first since I can. Then, I book airfare at 330 of my return home flight if available. Sometimes I wait until 10 months out for better airfare and schedule as i noticed sometimes the entire schedule is not released on day 330. This last trip I booked a red eye to WDW and then, I was going to use SW to home. Total epic fail, SW did not release any wanna get away airfare for my travel day. I was so bummed as I could have gotten a cheaper round trip airfare many months earlier.
I usually do both together, but airfare gets settled first as there is only one direct flight on one airline and SYR is notoriously expensive.
We had our first exception, however. We are going for Christmas, so I booked the resort at the 11 month mark and then booked the JetBlue direct the day fares came out. Prices have only gone up since then.
DVC first then airfare. I reserve our villa as soon as our booking window opens and then book air. I prefer a direct flight and usually find lower fares by booking early. Booked a last minute cruise last year and air was $$$!
ditto
it is usually harder to get the villa we want (BWV studio, BW view during the F&GF and F&WF), so we have to book accommodations early.
we book air as soon our dates come out, using SWA RR points (have SWA CC). i rebook if the fares go down, and the points go back into our accounts without any expiration or passenger restrictions (unlike "cash" bookings).
a recent "blip" is that SWA has reduced flights out of our preferred airport (ISP), so we have had to tweak our DVC reservations (usually waitlisting) or pay twice the RR points for flights on certain days/times.
DVC first, I like to know I'll have a place to stay before I book the travel to get there. Also because DH and I travel Southwest almost exclusively (DH travels a lot for work so tons of rapid rewards points), we generally book our DVC months before the air schedule is released.
For our November trip, the prices are still high and we realized it was cheaper to add a room for one night at POR with cash than it was to fly the day we check out of SSR.