Cashman inherited greatness from Gene Michael and Bob Watson who put together the Jeter Mariano dynasty. Now it's this 100% wedded to analytics/launch angles with no player development at the major league level.
They either should've gone with the kids infield this year or signed the big time free agents, instead Cashman brought in IKF and Donaldson. Bader is the one good move he made I can think of. If they keep Cashman and give Judge the 10 year record money challenging contract he's looking for they'll be doomed for a long time. He's an amazing regular season player but you're going to have everything tied up in a 31 year old injury prone player who stinks in the playoffs.
Boone is horrible but the biggest problem with this team is Cashman and the brain trust, if they're not gone they'll continue falling short and seeing players stagnate or regress at the big league level.
Bring in a real GM, someone like the guy in Tampa who always does more with way less. Get rid of Donaldson, IKF, Hicks, Torres, Chapman, Britton etc. Build it around the young guys you have and let the new GM trade and sign what they need.
Do I expect any of what I posted to happen, no because Hal is the baseball version of James Dolan.