Need advice.
Booked a flight back in December for May, JFK-SEA. 7:30pm Friday. Return on red eye Sunday night.
Details - my wife and I prefer not to take time away from work unnecessarily. We live N of the city near SWF.
7:30 flight canceled and merged with 6:30 due to schedule change. Highly unlikely to get off work at 3 and make it to the city and to JFK in time even with no checked bags and OLCI.
Alternative - Called DL and they said could fly out of SWF due to the schedule change. For the flight out this means a connection but the timing is perfect. For the return flight the earliest we could get back is around 1:30pm, which means a whole day of vacation rather than half day.
other alternative - fly out of SWF and return to HPN. Would DL consider that? We're going to use 1/2 day vacation anyway for Monday morning so instead of taking the train from JFK to near Newburgh just take it from White Plains or have a friend pick us up.
Last thing to consider is possibilitybof voucher. From reports on here the 7:30p flight JFK-SEA is often oversold as it's operated by a 737. The 6:30 is now a 757 and the red eye the same. Think it's worth the hassle to go to JFK for possibility of voucher or the larger aircraft negates it? Any experiences of VDB from SWF?
Thanks for the tips and any insight.

Most of the questions you've asked are things that only you can answer. Is is worth going out of your way for a possible voucher? For me, definitely not. Then again, if it were me, I'd just take an extra day off and make life simple. You clearly have different priorities. Only you can decide what is worth it.

I will say DL is being unusually generous allowing you to change airports for a rather minor schedule change. If they allow you to change airports on your return also (which presumably had no schedule change), then that is extremely generous. I would take it before they change their minds.

Why not change the flight out but leave your return as is? There's no law requiring you fly in and out of the same airport. You can likely Uber to the airport and take some sort of transport van home from JFK on your return. If you need to drive yourself to the airport, you can also rent a car on your return and drive to the other airport, returning the car there. Most rental car companies consider all the NYC airports the same (no one-way drop off fee), even Newburgh.

I often fly in and out of different airport when in NYC. Even in other places, I fly into one city and return to another, like into Buffalo, spend a day there, drive to Syracuse, spend a day there, and leave from their airport.

I would not suggest you allow the chances of obtaining a bump on a flight 3 months away to affect your decision in the slightest.

Totally agree here. Even if a flight is severely oversold, it may not even need volunteers (if there are no-shows), or they may just need one, which won't work for you.

This is what I was wondering when I started reading the story.

As this is simply a service gesture, not any form of required acommodation, don't count on the next agent permitting the departure airport change at all.

If SWF works better, grab it immediately, ask about HPN once you have SWF locked in and be done with it. Chances are that you will get a solid "no" unless you want to pay the change fees + fare difference, but it does not cost you anything to ask.

Only you can evaluate the risk vs. reward of flying on a smaller aircraft which is more likely to misconnect / cancel and ruin your entire trip, vs. taking a couple of hours off work.

Voucher for a bump? That is not even worth thinking about now. DL may well overbook the flight, but overbooking has nothing to do with overselling. More often than not, inbound misconnects make up for the overbookings and there will be plenty of seats.

Just one point on this part. If you return to HPN, I believe you would need to be picked up. The trains that run to White Plains (not to the airport, but to White Plains proper) only operate on the east side of the Hudson. If you live near Newburgh (on the west side of the Hudson) there's no interconnection to those train lines without going down to NYC and transferring from GCT to Penn to Secaucus Junction.

If you live on the east side of the Hudson this point may be moot though it would depend on where you live, since White Plains is served by the Harlem line and the points closest to Newburgh on the east side of the Hudson are served by the Hudson line.

Thanks for everybody's input so far. Looks like the general concenus is to not to even think about possibility of a voucher.
The reason for the indiciveness on keeping the return to JFK is the amount of time it would take on the train to get back home after being on a red eye all night. If we flew both outbound and inbound from JFK we would park our car off site and then when land hop in the car and drive home. But that wouldn't be the case.
The thought of the rental car was a good one but I wasn't able to find any pricing that would allow me to pick up at JFK and drop off at SWF for less than $80.
The SWF-XXX-SEA, SEA-XXX-HPN I think is the best bet if they would allow it. Just wanted to see what others thought before asking.
We do love on the East side of the River so would not require going all the way back to GCT

I could see DL allowing a change to SWF-XXX-SEA//SEA-YYY-SWF but not allowing you to switch the return to some third airport such as HPN given that there's no schedule change for the return. Is there perhaps a RT schedule to/from HPN that would work for you, so that you would have HPN-XXX-SEA//SEA-YYY-HPN?

Does the later flight from JFK to SEA not work for you?

I tried calling DL to present my resolution to them but hold times close to an hour now. The last flight from HPN-xxx-SEA is at 4:29pm on Friday eve which wouldn't work for us.
We would definitely prefer the direct jfk-sea that we purchased but the last late evening JFK to SEA flight stops on April 30. May 1 the latest flight is 6:30pm

I'd wait a day or so. You won't need to wait on hold so long and when agents are less pressured, they might be more willing to try to help. Figure out what you want and then call at a good time, remembering that you're only entitled to make one change. Don't have the ticket changed and then hope to be able to modify it further for free.

Bad weather impacting large portions of North East so give it two days for everything to clear up.
On return drive - I understand concern wtih train but unless you land early you will still encounter traffic driving after 7am rush hour.

I constantly hear the plows going by. I was surprised when I called at 1:30 am today there wasn't a hole with the impending storm coming. Definitely going to wait a few.
I understand making everything at one time and not expecting changes again later.
The best option I think outside of the fly into HPN is the one way car rental mentioned earlier but cannot find that.
Does anybody have insight if that's possible. Car rental JFK-SWF w/no drop fee?

kayak.com shows JFK-->SWF approx $89 from Budget (picking up Mon 8 May)