At this risk of making this thread look like a SteveP blog, I'm going to throw out one more post, because I may have solved a couple of puzzles in my own mind about DS behavior.
1. I suspect that the total # of actual DS attempts IRL in 1960 was actually zero. I think that what I see in the game logs in that year, that look like DS attempts, weren't. Just guys on 1B taking advantage on their own of opportunities to steal 2B, while a play was being made at 3B. It's the only plausible explanation why a team like the Giants would DS one time early in the season, and never do it again. They never called a DS that time either. So, now it looks even more certain that part of the problem is era-specific.
2. But I also think it's probably not entirely era-specific. A true DS play (as opposed to an accidental, opportunistic DS) is a difficult, risky proposition. It requires coordination, a good call on what pitch to run on, avoiding one of the runners getting picked off first, doubling your chances of losing a baserunner, etc. Teams that develop experience with the play can reduce that risk, but it's still a daring thing to do.
Given that, my intuition is that DS plays in OOTP happen too frequently and too routinely, and teams get away with it too often, to realistically model the risks and difficulties of that play. As an analogy, I think that if gameplayers saw successful squeeze plays every 5-6 games during a season, they would think "whoa, what's this about!" In 1960, squeeze plays occurred quite often (about once in 20-25 games), but no DS. Food for thought here.
Again, I don't have data from a later season IRL, so not yet a complaint -- just a placeholder for a possible future complaint.