Still, Cheveldayoff hopes the negotiations gain traction and arbitration isn't needed.
"Logan Stanley's RFA is much simpler to work on because of the nature of his tenure," said Cheveldayoff, before shifting to Copp and Pionk.
Copp had a career year in 2020-21, while Pionk has had the two best years of his young NHL career in a Jets jersey.
"We love both players, and certainly, if we can find a way to do term deals with both of them, that would be the ultimate goal," said Cheveldayoff. "Where it sits right now, how it will play out, it all remains to be seen. The cap is very real and our contract situation is very real."
Oh yes, the cap.
The $81.5 million salary cap remains flat for another season, though with the addition of the Seattle Kraken, there is another team Cheveldayoff and the Jets have to negotiate against when it comes to free agents.
As per CapFriendly, the Jets have just over $7.7 million to work with. However, the actual number in-season will be a bit higher, given that Bryan Little remains unavailable to the team due to injury. It's expected he'll remain on long-term injured reserve, which gives the Jets some flexibility with that salary cap ceiling.
Speaking of Seattle, their claim of Mason Appleton off the Jets roster, plus the departures of Nate Thompson and Trevor Lewis up front, means that Cheveldayoff also has some decisions to make when it comes to other spots on the roster.
"I think that's still a little bit of a work in progress," Cheveldayoff said. "I still think there are some names on the board there that we do have a level of interest in and we'll see how that all plays out. It will be largely a function of available discretionary dollars to spend."
Names like Kristian Vesalainen, David Gustafsson, and Jansen Harkins played in NHL games last season and are among those that will battle for spots up front next season.
On the blue line, there may be less spots available for Ville Heinola, Dylan Samberg, and others, but that is what training camp is for.
"(Those are) good young players that are going to be a part of what we have going here," said Cheveldayoff. "Having this opportunity to grab those two players (Schmidt and Dillon) that help the top end of our defence right now is certainly something that I think will actually help those players get into the lineup.
"When they do, you'll have greater options to be able to play younger players with real sound defensive players as opposed to guys who are just trying to cut their teeth or play at the level that they have to to stay in the game."
That's the challenge of managing every day of an off-season for a general manager. One eye needs to be on the present, but the other is always looking ahead.
"A lot of the core is locked in, but there's fixed costs there now," said Cheveldayoff. "The reality of where our cap is today and what it is going to be moving forward, and again, we're probably living in a flat-cap environment again next year, so when you're doing future contracts, you have to take that into consideration. Our balance sheet looks much different than it did 24-48 hours ago."