So some of it is luck- sometimes they just throw you out. But I’ve gotten it with 50 speed guys on bad throws too.
Make sure you have at least one or two fast/SB guys on the bench so you can pinch run. Even if you didn’t draft them, the game will usually give you at least one usable pinch runner type in your pool of players
Take a perk that helps with stolen bases - you can always check by backing out of the draft screen to see what the next showdown scenario is before picking, unless it’s the first one.
Don’t go on the first pitch, just take it. Seems to work better for me to go after you take one.
Learn to hook slide