In theory (I feel like "in theory" should be boldfaced, 20 pica, italicized, underlined...)
When TK hits UFA, we'll have Cam Atkinson off the books if we haven't traded hi yet. Same with Hathaway. Depending how long and how much of a deal we sign Tippett, Poehling (if), and Brink to, we should be able to swing it. Sean Walker, Staal, and Seeler combined don't give us much more runway. I guess the heartburn will be the Hart contract, but he'll be RFA so it's still manageable unless he only extends one year.
It's the Couturier contract that will be the albatross by then. 25-26 should be the year we're going for it "in case" some of these necessary signings don't pan out and it sets us ack. York will be an RFA at the same time we're attempting to sign TK, so that could be a thing. Petersen comes off the books, though, so maybe it all pans out.
I'm glad I don't have to track/gameplan this crap for my job, though.