I could definitely see him trying that route but I feel, with the way they keep improving, they should try to lock up to long term deals. I feel 7.7 for Raymond and 8.7 for Seider would be reasonable.

I agree they should try and get them on 7-8yr deals, but if you want to improve this team next season and moving forward, they have to move a player or two via buyout or trade. Ik this goes against some wings fans, but I would 100% start hearing what other orgs would trade to get jake walman. Yes he scores some clutch goals, but he is not a top pair dman, does not tie up players well on the pk, and same with Hronek you want to trade him before he asks for a ridiculous contract and you get something in return outside of what hes done for the org on and off the ice. Then of course you have Petry, Holl, Fabbri, and Husso to name some. Out of all these names, Walman would get the highest return possible outside of cap. This would create room for Edvinsson, Chiarot and Seider top pair seems to be working for now, and the team has gone back2back wins without him in the lineup, and i believe theyve lost only once with walman out of the lineup.

Long rant story short, if we want this team to improve, and sign seider and raymond to those long term high dollar contracts, you gotta move some pieces one way or the other.

Chiarot and Seider didn't work well pre-Walman, but I think with Seider improved that it could be viable. I agree Walman isn't the ideal top pair defenseman but right now he's the best we got. If we move him, we take a major step back. I would be waiting until next trade deadline at the earliest to see how Edvinsson does with a full season. If he could step in and fill that hole than for sure. With the term on his contract, we can afford to wait.

As for the contracts, I think it depends where they see this team in the 3-5 year range. If they are willing to sign for 4-5 years and Yzerman sees this team as a true contender in that time frame, then they definitely should. Those contracts would provide huge value at that point. If Yzerman doesn't see this team as a true contender in that time frame, then we should be trying to get long term value contracts signed. Ideally something that, although not quite worth it right now, should provide really good value in 3+ years.
I also feel, with the UFAs they signed and the contracts handed out, that very few of these players would be considered core players and are in the long term plan. The only players I consider to be long term core players for this team, that are currently on the roster, are Larkin, Raymond, Seider, Edvinsson and possibly Debrincat. The rest, including Walman, are short term stop gap fixes until they have internal options ready.
I still feel this team has a long way to go before they are a true contender but improving the team now is obviously important.

Don't have to think Yzerman would go this route at all.

Difference between now and when Yzerman signed Hedman and Kuch is the cap didn't get held back for four straight seasons. Starting next year the cap is about to propel forward at max increases for probably the next five years, minimum.

Zero need to sign Seider to a 5 year deal and put him right into UFA at 28 with a ~$105M salary cap. Great way to put yourself in a position where he's demanding $12M - $13M.