Mike, I can't recall any wording like that in the book since I've started umpiring, but I think 8-5-B-2 covers it very well...
Quote:
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EFFECT: A dead ball is called and the obstructed runner and all other runners shall be awarded the base or bases which would have been reached, in the umpire’s judgment, had there not been obstruction.
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While it doesn't use the same language you used, I think it's clear to me that if your judgment tells you that R2 would have clearly made it home had the obstruction (and resulting dead ball) had not happened, you should award R2 home.
Maybe you heard it phrased like that in a clinic or school? If so, I can't say I agree with the wording. I don't have a tape measure with me on the field, but it's my judgment based on what I see that determines "s/he would have or would not have made it home safely if there had been no OBS at 1B."