I believe a team can not offer a QO if they buyout a contract. However, if a player has an opt out and does, a team can offer him the QO. I could be wrong on that first part though.
He got fired from ESPN back in the day for sexual harassment right? So did Steve Phillips and both are employed by MLBN. Aren't there plenty of ex-players/coaches/GMs where they wouldn't need those 2?
If he keeps hitting, no I don't think May/June of next year is crazy. Obviously, if he starts struggling as he moves up then you would re-think it but so far so great.