https://blogs.fangraphs.com/the-yankees-need-a-remake-but-their-flexibility-is-limited/
Fangraphs has a good summary of the Yankees situation, and in general I agree.
I'm writing all of this with the assumption that ownership still wants to be around the CBT level every year.
I would add to the Fangraphs article that things, to me, feel a bit desperate for the Yankees and that's primarily related to a lack of cost-controlled upper tier talent. In 2017, when the Yankees surprisingly won 91 games and made the ALCS, you figured that a good six year window had opened up because of how many cost-controlled young players were already in the team or expected to graduate. You guys had Judge, Sanchez, Torres, Severino, Bird, Andujar, Frazier and others who could reasonably be expected to maintain or improve on their 2017 level. And, true to expectations, the majority of these players lived up to the billing. You guys had two 100-win seasons even with some injuries. Because you had all of these cost-controlled players, you were able to spend heavily on the bullpen and the rotation to compete, and compete you did. From a roster construction perspective, Cashman did very, very well.
But now we're heading in 2022, basically the last year of the six-year window, and things feel desperate because a lot of these young players are getting close to their payday, and some could be said to be passed their physical peak if you accept the typical MLB aging curve. Judge, Cole, DJ and Stanton are passed their peak. This had to happen, of course, players will get old. But the situation is desperate because the Yankees have basically not graduated any upper tier talent for a good 4-5 years. At this point, the 'smart' strategy would be to accept that you are going to lose some talent from the team, go into a soft 2014-2015 rebuild, push guys up as quickly as possible to see whether the talent translates in the majors. For example, Schmidt, Deivi and Gil should be starting next year, or get multiple innings from the pen regularly. If they perform well, with the remaining base level talent of the team, you're going to win 95 games and continue competing. If they don't, so be it, at least you know what you have, trade guys at the deadline for some prospects and target 2024 as the start of a new phase. This includes trading Judge at the deadline next year, if the team is not competitive.
The key to contending again year-in year-out is to get upper tier cost-controlled players. From a timing perspective, doing a soft rebuild now is would also fit the timeline of the AL East. The Jays and Rays are going to be dominant for the next 2-3 years, winning 90 games and losing at the wild card or ALDS every year whilst not stocking the farm would mean trouble in 2023 when everyone has fully aged out of their peak and it would put a lot of pressure on the farm to graduate some really good players.