I've generally thought that the Jets never should or would let Scheifele and Hellebuyck play out the 2023/24 season and then leave as UFAs.
I still think it is very unlikely (based on the Jets' past approaches with Ladd, Trouba, etc). I also think that they would be wise to try to get the best return back for both, even if it's less than many had hoped, considering the unpredictable market.
However, I don't think it would be the end of the world if the Jets look like a strong contender and decide to keep both as "own rentals". Part of the reason is that I value next season as much as any future season, and realize that Cup runs are often unexpected, especially with a hot goalie. Also, the worst case scenario is that the Jets have to go with a full youth movement in 2024/25, which will coincide with the last seasons for Ehlers, Iafallo, Schmidt and Pionk.
If the Jets are into a full rebuild in 2024/25, they will have a passel of young players ready to contribute (McGroarty, Barlow, Lucius, Lambert, Chibrikov, Zhilkin, Salomonsson, Heinola), and they will still have a ton of trade capital to aid the rebuild (Connor, Ehlers, Lowry, Iafallo, and TDL rentals like Schmidt and Pionk). In essence, if the Jets go all in this season with Scheifele and Hellebuyck, they would be deferring a full rebuild by a year, and starting when they have more prospects ready for NHL roles. Just a thought.
But there's another path, too. Keeping Scheifele and Hellebuyck doesn't mean they can't re-sign them next off-season. They'll still be in the driver's seat, and if they have a strong season I could see at least Scheifele considering an extension.
So, I'm not sure it's as cut-and-dried as I and many others have been thinking.
Still, I think the most likely future is the Jets trading both 55 and 37 between now and the TDL, if they can't extend contracts.