PG,
I'll say again that it really has to be taken on a case by case basis. If the pitcher looks sharp, is throwing strikes and is throwing first pitch fastballs they'll have the green light. If the pitcher looks fatigued, has not been throwing a lot of strikes, has been going off speed on the first pitch fairly often then I'm probably going to have the hitter take. It also depends on the hitter. A kid who tends to swing at bad pitches will be given the take sign. A kid with a good eye will be allowed to swing.
As far as the 95% success rate kid on first, I'll have the hitter take a pitch while that kid steals. I'll trade eliminating the force at second and the double play against the 1 in 20 chance of being out. I wouldn't have an 8 of 10 kid steal.
On the other hand with 2 outs and down by 2 the baserunner is not stealing.