This is just my opinion as to how I might approach the offseason if I was Chevy. That being said, I think they have done a very good job putting this team together.
Here is where I would start, with the guys I'm considering as the "written in pen" types:
Connor - Scheifele - Vilardi
A - B - Perfetti
C - Lowry - D
E - F - G
There are lot's of internal options for all the un named spots. And honestly, I do expect 99% to be internal. I'm just starting from a blank slate, maybe a more "wishful" perspective.
A - Options: Ehlers, or internal options like Iafallo or Lambert, or possibly go out and get a UFA. I hope something can be worked out with Ehlers.
B - We're not unique in the NHL looking to get a top 6 centre. They are hard to find. I don't think signing a UFA is super realistic. It's most likely that Names is in this spot again next year. The other potential option is looking for a team looking to pivot to a rebuild. In a pie in the sky, not going to happen example, a team like the Islanders who might want to trade players for picks and prospects and a guy like Barzal or Horvat becomes available, etc.
C - Most likely looking at Nino in this spot and he'd been a good fit, but age is starting to creep up. At some point the team may want to start looking at putting more offense on this line to go along with Lowry. So most likely Nino, but possibly Iafallo as well. Very outside chance of a UFA here IMO.
D - Even without the recent miss from Appleton, I was always of the opinion that his salary in 2025 would be hard to afford. And with Iafallo signed, I'm not sure if extending Appleton is the best use of cap space. Other options in this spot include Rashevsky, Chibrikov, Lambert, or Barron.
E F G - These spots IMO are up for grabs and it depends if anything changes in the top 3 to see who is available. If someone is brought in to replace Names at 2C then Names would be excellent as position F. Although that is not super likely so I can see Barron being a good starting point for F (with Gus as a backup). E and G also depend on what happens above. If another top 6 winger or two are brought in, that could move Iafallo down. Or you could possibly try a Chibrikov here as well.
Morrissey - H
Samberg - Pionk
I - J
H - 99.99% it's Demelo here, just not putting him there from the perspective of, if there was someone available that would be an upgrade that the Jets could acquire, it might be a good position to upgrade.
I - Stanley and Heinola are signed. It doesn't seem like Heinola has much confidence from the coaches, and Stanley is well documented. Signing Fleury and moving on from one of the others might be an idea.
J - We have both Schenn and Miller signed and Salo waiting in the wings. Depending on how TC shakes out, or how the management group graded Salo, I'd probably look to move Schenn ($), and run Salo and Miller there next year. We have to see if Salo can take the reins.