Base Stealing Viability

There are some owners who always set their stealing setting to conservative or very conservative, because they "don't want to run into outs". They may also apply that to baserunning.
I am not so sure that that equates. A successful steal, puts a runner in scoring position, and avoids the double play, those are not insignificant factors.
If you have a team with a majority of 1-17, 1-16, 1-15 runners, then going for the XTRA base makes eminent sense.
Someone suggested that it would be great to have individual base running settings, ---i.e. so your 1-9 catcher doesn't try to stretch a double. Thats a great idea. Maybe it does not have to be individual, but the setting could be based on a cutoff for runners such as this:

1-14 and higher:
Below 1-14:

High speed teams, like base stealing teams, put runners in scoring position and take the offense out of DP sitches.

There has to be an equation that determines the numeric advantage/disadvantage, but I flunked math so I wouldn't even know where to start...

Interesting. I heard before that anything less than 80% successful steal rate was disadvantageous. I didn't realize stealing somehow reduces double play potential, can you elaborate?

I admit I've struggled to assign a specific value to the catcher's arm and finally just go by gut feel.

Henry can be a good catcher but it's really frustrating to watch players end up on third base after a walk.

New base stealing question:
Some players have a steal rating like this: E 2/- (20-6)
It seems they would not be held on.
So, I would uncheck the "Don't steal" box and expect them to get an occasional free base when they roll the 2 (good lead).

But whenever I've tried this, they always seem to end up with 1 SB and 3 CST.
Although I want them to steal only when they get a good lead (20), it seems they also steal sometimes without a good lead (6).

I've given up on this strategy and just check the "don't steal" box. Anyone ever have success trying this?

New base stealing question:
Some players have a steal rating like this: E 2/- (20-6)
It seems they would not be held on.
So, I would uncheck the "Don't steal" box and expect them to get an occasional free base when they roll the 2 (good lead).

But whenever I've tried this, they always seem to end up with 1 SB and 3 CST.
Although I want them to steal only when they get a good lead (20), it seems they also steal sometimes without a good lead (6).

I've given up on this strategy and just check the "don't steal" box. Anyone ever have success trying this?

Whenever you try for a lead there is some combination of rolls/splits that results in a pickoff. I don't have the energy to look this up, but I've encountered it in the windows game. I wonder if these pickoffs end up being counted as caught stealing.

I looked up the super advanced rules, here's what it says:

If the 20-sided roll is 1, the runner attempting the lead may be picked off. Refer to the runner’s second steal success rating (in parentheses) and roll the 20-sided again. If the number rolled is less than or equal to the runner’s rating, the runner dives back safely, but has failed to achieve his good lead. If the number rolled is higher than the runner’s rating, the runner has been picked off (statistically, this does not count as a time caught stealing)

So if this is accurate, I can't explain where the caught stealings come from. Anyway, with a 2/(20-6) stealer, you have a 1/36 chance of getting a good lead and a 1/20 x 14/20 ~ 1/28 chance of getting picked off.

I don't fully understand the pickoffs either, they seem to happen more than I anticipate. It would be so great if we could get more clarity on how this all works, I'm generally pretty happy with the game but base stealing has always seemed to be a bit disappointing. I know I can't be the only one as there are a lot of teams with abysmal stealing numbers and it really shouldn't be this extreme. I think if things were more clear we'd see it in a better place.

I don't fully understand the pickoffs either, they seem to happen more than I anticipate. It would be so great if we could get more clarity on how this all works, I'm generally pretty happy with the game but base stealing has always seemed to be a bit disappointing. I know I can't be the only one as there are a lot of teams with abysmal stealing numbers and it really shouldn't be this extreme. I think if things were more clear we'd see it in a better place.

The stealing system is completely transparent, what are you unclear on?

New base stealing question:
Some players have a steal rating like this: E 2/- (20-6)
It seems they would not be held on.
So, I would uncheck the "Don't steal" box and expect them to get an occasional free base when they roll the 2 (good lead).

But whenever I've tried this, they always seem to end up with 1 SB and 3 CST.
Although I want them to steal only when they get a good lead (20), it seems they also steal sometimes without a good lead (6).

I've given up on this strategy and just check the "don't steal" box. Anyone ever have success trying this?

Yeah as djmacb detailed the steals from these guys aren't worth the pickoffs. Although I don't believe pickoffs should be scored as CS? And I doubt those guys are running without the lead, so those CS must be from when they're running against minus arms, reducing their safe chances.

If pickoffs WERE scored as CS that would actually be helpful and edifying IMO.

@MaxPower Specifically, I would love to know what Steal More and Extra Conservative to Very Aggressive means. If I'm not mistaken, Extra Aggressive makes the runners try to steal home significantly more frequently. I can't say for sure as I rarely use the setting, I find it to be far too risky.

Ah right, true, that part is murky.

Personally I turn stealing off for everyone who I project to have a lower success rate than break-even, then leave the team setting on Normal. Haven't noticed any attempts to steal home with those settings.