"steal more"

Does this option simply lead to a reduced success rate on my steal attempts? If so, what is the "penalty?"

I've been operating under the assumption that it sets the player in question to the next level up of basestealing aggressiveness vis-a-vis your team settings. E.g., you set your team to "conservative" but set Ty Cobb to "steal more", he will behave as if your team were "basestealing: normal." Anyone happen to know if that's right?

Either way, setting my team to conservative, checking the do not steal box for my crappy runners, leaving the boxes blank for my decent runners, and checking "steal more" for my very good basestealers has worked quite well for me. I don't think it reduces the success rate on a given steal attempt at all - it will lead to more attempts in general, which means more stupid attempts of stealing 3rd, which I see as the main tradeoff.

I agree.

I never use "steal more." I would use steal more quite a bit if there was also an option to never steal third.