The way i see it is this, with beppe we had reached his ceiling with us in his last couple of years. We had 2 choices, settle for being an italian powerhouse that could never rub shoulders with the euro elite, or take a gamble and go all in to close the gap, we chose the latter and for many reasons we came up short. I personally would always go for option 2.
Now to answer your question, beppe never was successful without conte. He has definitely a knack for getting good, emphasis on good here, players on the cheap. Would i take him ahead of cherubini, yes i would because in a rebuild you can't really gamble imo.