I initially liked Chayka's signings and deals. Upon reflection, I've tried to figure out why - and then I realized it. His deals were the kinds of deals I do when I play Eastside Hockey Manager. In fact, the Raanta/Stepan deal was one I did myself playing the Coyotes GM in one of my EHM saves, which is likely why I was such a big fan of it at the time.
But over time and with hindsight, I realize what the critical issue is with the way I play a hockey management game and how John Chayka played as GM. See, unlike baseball, where data analysis and advanced statistics are a great way to find value in players because of the nature of the game, hockey is a visceral game, played as much with the gut and the heart as it is with the brain. So, so much of hockey is affected by human impulse, instinct, personality, and chemistry. In baseball, the most complex interaction between teammates is something like a relay throw from the outfield to start a double play. In hockey, every single interaction with the puck is a multi-person effort.
In EHM, it's easy to find good players and players with potential because the game boils everything down to set characteristics and personality values. There is very little randomness to it. Other hockey games have tried to change that, but with only limited success thus far. In EHM, I can dump Jason Demers' contract for a couple of late draft picks; the game decides that my owner and fans don't like it, but I know that with Demers at a -18 and playing poorly, it's addition by subtraction. In real life, though, Demers could be playing like crap, but his personality in the room might be the only thing keeping Conor Garland focused on his game (I'm saying this theoretically, of course).
Chayka never seemed to get that. He approached being a GM like the human element didn't exist - as if the players were commodities that were easily summed up in a one-sheet EHM-style player report. That's where I think he failed - everything he did looked good on paper (or on a screen - sorry, young folks!), but I question how much thought he put into intangibles.