I am firmly in the approve camp as the positive moves he has made outweigh the negatives.
Obviously the dickey trade was a huge error but the way he has rebuilt the farm system twice in a way that JPR never could is a massive plus for me. There's no way we could have dreamt about trading for JD, Tulo or price 10 years ago.
I enjoy the buzz he has created around the place at several points in the last 5 years, particularly with the high profile trades this year. I think these outweigh the negatives of poor bench management as it is much more impactful.
Also, I think we underestimate how difficult it is to create an effective roster when working in Toronto & you have a limited chance at snapping up top free agents. I think he had done extremely well to create one of the best teams in the AL through his drafting and subsequent trading.