You are double-counting. AD Benedict knew the situation, knew the unhappiness of the players and interviewed all of them, must have known several were considering transferring and why. You can't count the transfers and the decommit as post-retention decision events.
As for this year, what is surprising about it? With Gilbert there was some hope to become an NCAA bubble team, but without him we're a kenpom #100 team at best and can hope to reach .500 and make the NIT. The team is playing to expectations so far. Unevenly, to be sure, but about as expected. How many teams finish above .500 that lack a center, lack a point guard, lack 3 point shooters, have all-freshman forwards, and lack experience playing together?
As you say, the team has to show cohesion, heart, progress, and signs of good coaching. Another post-season of discontent would be unacceptable. But if the team progresses like a normal basketball team and returns like a basketball team, then I think Ollie gets another year.
Bottom line for me: Ollie has shown once before that he can coach a complete roster with good players to the highest success; and he's shown that with his Chillious-led coaching staff he can recruit effectively. Thus there's reason to hope that we'll in time once again have a complete roster with good players, and we may see them then attain high levels of success. But, it's all dependent on player development and building a team. Let's watch and root for him.
