Lucchino was in baseball for a billion years - and was super experienced building a front office. He clearly was well heeled in EVERY aspect of the baseball business. Remember, Lucchino was Epstein's mentor - he discovered him, and helped pay for Theo to go to law school. I think at a certain point Lucchino could not let go - he was the president, he wanted his say on moves. This was not an unreasonable belief - and so it resulted in some moves which there might not be 100% agreement on. This obviously also applied to Cherington, who also came up the same way.
Now Epstein has every incentive to spin his side of the story - it's easy to say ex post that "hey, I would have taken a different approach". But - he was part of a collaborative process, and some of those moves didn't work. Also, I'll submit that all of the moves were not ex ante bad moves. I mean the Red Sox ended up in one offseason signing the top rated pitcher and the top rated position player. And then they made a trade for one of the best power hitters in the league squarely in his prime. Basically injuries (and the ability of the players to deal with them) caused all three moves to be sub-optimal, but all of them made sense. Crawford's failure was obviously more than that (specifically that one of the league's best defensive players went straight into the tank on THAT end).
The one thing Dombrowski did (and Henry allowed) was that he is clearly where the buck stops in the front office. Given how accomplished a baseball guy he is, that is not a bad thing. And - by all accounts - he did not just willy nilly destroy the business processes that were already here. (a front office which was the envy of the league) After all, on paper he should NOT have been attracted to Cora - or anybody from the Astros shop - but there you go.