I think the answer to this question is more simple than one would think.
They can make mistakes, they can hit home runs, but that's not the true measure of success.
The measure of success is results. This is pro sports, not the Participation Olympics.
If they're an elite team with a sizeable window in 5-7 years, then they will have succeeded. If they are not, then they will have failed. Till then, we'll nitpick every decision they make because that's what forums are for. If they make a string of consecutive idiotic decisions, we're likely to notice things aren't on track.
As for the current team, I like a lot of what they've done on the management and development side. I also like that, in a lot of cases, we're aligned with their decisions and those decisions seem to make sense. They've also been somewhat transparent and candid so far with their reasoning on things provided we can take what they've said at face value.
Here are some things I don't like:
-The Bobrov hiring and keeping on Lapointe.
-The Slaf pick smacks to me of dinosaur hockey mentality and trying to be the smartest guys in the room. I don't know how that will work out.
-WHY IS BURROWS STILL HERE
-Unwillingness to say they'll commit to a full rebuild, which I think is Molson's doing