So here's exactly what you need for the achievement (i just did today)
I should not have to say this but before anything make sure game is on Pro and do not change any GAME sliders
1. Enter the MYVIP menu and turn on classic batting(from the settings).
2.Go to the cheat input section and put "Derek Jeter" (cap sensitive)
3.Go to the cheats list and turn on Super Bunt, Diamond cutter and two strikes Yer out!
4.Go to the rosters and Find the team you play as(i personally picked the yankees) and raise all of your batters Sliders for stealing all the way up
Now Select Play ball(or game w/e) and pick your team, change the opposing team to the Florida marlins.
Pitch until you get up to bat...then do this
When they pitch the ball hold Y it will bunt(sometimes it does not hit but most of the time it will) and get to first base.
When you bat with your next person, hit B and you will be controlling the man on base, then hit left on the D-Pad to select do not swing).
Now here's where you have to pay attention, Watch the pitcher before he throws the ball he will lower his arms...when he does this get ready and AS SOON as he raises his leg to pitch hit right trigger and tap A like a madman, this will allow you to steal 2nd,3rd whatever
If done right you will be on the next base and it will say safe, this counts as 1 (you can steal 2nd and third base, though ive never stolen home and would not recommend trying)
just rinse and repeat this in a 9 inning game and you should get it pretty early
it will take a few trys but when you get the hang of it its very very easy. If you have any questions you can message me and ill message you ASAP