When they have combined 130 SB between them, I think it is. Especially when the batter is high contact.
But it's not just that one situation. It happens a lot. I try and do 5 H&R and avoid DPs and advance runners against dead ball pitchers with high contact guys and the SIM doesn't do a H&R when they should.
It's frustrating. I'd rather play LIVE more but I can never get anyone in my season to do so.