To make this less of a grind be the yankees and get your level 30 achievement, which should take less than 10 years. After that concentrate on the first time series winners by getting fired after you win the world series with the teams that are hiring when you are looking for a job. I was able to knock out many of the team achievements with my high level GM. Makes this game much easier. Plus winning the world series for consecutive years will make you a historic GM. If you sim all 30 years and dont win alot you will be a failure and no cheevo. hope this helps.