Hi Jeff, I am not sure what goes into selecting the manager of the year, but in two separate games in Challenger Mode, I have GM'd the Canadiens from perennial also rans to five-time consecutive Stanley Cup champs (in one case 7 Cups in 8 years) and never even been nominated for Manager of the Year.
Also, three times in those championship runs, I was automatically re-signed at the same rate (I even became coach twice and received no new money), which is a problem.
1) Perhaps the game could give out $$$ bonuses for success.
2) GMs have agents, too. It would be good to have an agent send an email saying "if you don't re-sign with the Habs, these teams would definitely be interested in signing you once your contract expires." Have a little bidding war.