I've been playing for about 2 weeks straight now and can't seem to finish the achievements. My season keeps restarting even if I haven't traded anyone and I can't seem to beat last seasons record. Wanted to do everything in the game, but this is making it impossible. Had a lot of fun though.
The season resets every 162 games. This should affect achievements however. All achievements are taken from the lifetime stats of the players or the organization. Some of the achievements may be too tedious; I've toyed with the pace of the game a bit since first release without giving as much thought to readjusting achievements in response.
In any case, I'm glad you had some fun. Thanks for giving it some of your time.