My biggest complaint about him is that he brought an NBA perspective to the NHL and was never a hockey fan. But I have to concede that he's become much more concerned about the importance of the game's traditions. Some of the changes that have been made in the NHL over the years -- like the Winter Classic, the Christmas break, etc. -- have been very positive moves and should be a positive aspect of his legacy.
Yeah he had a steep learning curve but he actually learned. After some pretty big early missteps he’s done some really good things. Heck they finally have a long term TV contract, and it even pays them some half way decent money, OK it’s still probably the worst national TV contract of the major sports but they’re getting cash upfront and have stayed on the same networks through multiple contracts each. Plus all the stuff you mentioned, love me some Winter Classic, and Hockey Day in America was pretty cool too.