A much easier approach to these first time world series winners is to reach level 30 with the yankees and then release all your star players and simulate a few seasons. You will be fired and then be able to choose between a few teams and i was successful in having the teams necessary for these achievements more often than not. Also i would save at the end of each regular season then simulate the playoffs as you are immediately fired after the world series and must choose a new team. I was also able to reload from the end of the season and get additional teams as new options to coach.
This option is not guaranteed to get you all team achievements but when you get a needed team you can easily win the world series by simulating the entire season. Just make sure to free up cap space by trading expensive players and sign young cheap high rated players because having a GM that is over a level 30 gives the team an immense boost to your players. Worst case is you may have to save and load 20 wins in a season instead of reloading thousands of times because you keep losing every game. Hope this helps message me if you need help.
edit: create multiple saves too