Could be. But the Yankees have shown you can rebuild quickly.
Who knows. Honestly, what are the players going to give up to get that change? Big contracts?
To be fair the Yankees had like 2-3 years of total mediocrity (bad for their standards) while they were rebuilding, and also changed their player development pretty substantially. Their trades were also incredibly well-done and creative. It'll be tough for Rizzo to do the same here. They had 3 first-round picks in 2013 that led to Judge, a trade for Chapman (Jagielo) and a trade for Robertson/Kahnle when they needed help (Clarkin). There's no Clint Frazier or Gleyber Torres out there for us.
And I also think that in the new CBA Super 2 won't be a thing and either arbitration hits earlier or free agency hits earlier. Either way, service time shouldn't be a concern IMO.