I got 3 points in the first inning, unlocked this achievement but no other
Reset the game because they wouldn't unlock (closed game and re opened)
Hit a home run, got the 1st caravan achievement
Hit a grand slam and the 2nd caravan achievement unlocked.
So if you get 3 points first, close and reload your game if the other achievements don't pop. The game glitched and wouldn't unlock ANY other achievements until I did this.
Pick American dreams, and aim for getting at least a home run in the first round. If you click X shortly after you select your team and the enemy team is spinning, you get good odds of getting a weak team. Good luck