Next year actually feels easier than the year after that. If you run with Woll and Hildeby(or some cheap equivalent) then you've got between 12-16 million to improve roster holes like 2 LW and 1 RD pending how much you give Liljegren and if you are able to trim any of the fat lying around on some contracts we already have. Sure the year after that Tavares is up and more than covers any Marner raise. However Tavares + Marner + Knies + Woll + McCabe currently cost $25,594,667. Assuming any major additions this offseason aren't single year contracts those are your big FAs during the summer of 2025. Do you fill all those holes for cheaper than that?
Lets say Marner takes Willy's deal, and Tavares gives you a discount to fill the 2C hole at 5 million(I think Kopitar/Giroux kinds of deals are reasonable on the open market) that leaves you just over 9 million to fill McCabe's spot and for Woll, Knies extensions. The cap will go up, perhaps 4 million in that offseason as well. While I'd rather not do it I expect a bridge deal for Knies. Lets say 3 x 3.5. Woll however will be 1 year from UFA so any cheaper short term deal makes him a UFA. Not that that's a bad thing perhaps, we're now happy that's the route we took with Samsonov. If he's earned it by then a long term Woll deal might look like 5 x 5. That leaves you with a hair above 4.5 million to fill McCabe's 2nd pair spot which won't be easy. This is also a positive outlook. Perhaps it takes 12 to sign Marner, and Tavares gives no discount. Sure we let him walk but a 5 million center to replace him won't be nearly as good. Bridging Knies is fine but they might want to go long term. Not great when your hand is forced to go bridge.
I'm saying all this to say the easy thing to do is to say next year is a squeeze and we're fine after that. After all next year will be the year where 4 guys are making 10.9+ million, then the least desirable one drops off. But there's some raises coming to 3 very important roster spots in 1 LW, 2 LD, and 1 G. They'll still be fine of course. It'll work. But those 3 cheaper roster spots actually make next year somewhat easier than you'd expect, and those raises will make 2025-26 somewhat tougher than you'd expect.
I agree with you and have posted similar to this myself. There are a few "ifs" here, but every team has them. I am not suggesting that we have more than other teams, I am just listing a few of them here. In order for this team to continue to have regular season success and improved playoff success we need:
Matthews and Nylander to continue to be two of the best players in the world.
Rielly to continue to be a top pairing dman for another 3 to 5 years.
Marner to continue to be a top two way player and to sign an extension similar to the deal Nylander just signed..at worse, Nylander money and Matthews term.
Tavares to resign at $5M or less AAV.
Knies, Woll, and Liljegren develop to top 6, top 4 and starter while signing reasonable extensions and bridges.
Continue to identify, sign and extend NHL depth at low value contracts. This includes guys like Gregor, Benoit, Jones, and Lagesson.
Attract, resign and retain veteran depth on discount deals like we did with Spezza, Thornton, and Giordano. This might include guys like McCabe, Brodie, and/or Tanev.
Develop a pipeline of player that can contribute on ELC or low value deals. We don't need ALL of those guys to hit but we need a few of Robertson, Hildeby, Holmberg, Cowan, Minten, and Niemela to hit.
Avoid signing bad long term deals that we will regret (we currently have none). The above would be a recipe for us having our core, our depth, our youth and $15 to $20M in cap space in two years (go to CapFriendly and see for yourself) for a 2LC, a top dman and or a goalie.
Next year is the tight year, but not too tight with so many guys coming off the cap and LTIR.