I thought the OBS rule/penalty was to negate any disadvantage to the runner resulting from being illegally impeded.
If so, there is no nesessity to decide at the moment the OBS occurs which base will be "awarded". We don't know what the runner and fielder will do.
Temporarily ignore the possible dead ball caused by an apparent put out. After action ends, judge whether the runner has reached the base which would have been attained with no OBS and if not, "award" that one.
The judgement of which base would have been reached includes how substantial the OBS was and how close the play was on an attempted put out. For example, runner from 1st obstructed before 2nd on a ball hit to the deep outfield. The runner keeps going to 3rd and is apparently put out on a very close play. The runner is not protected by the "bases between" clause, but should be awarded 3rd if the delay caused by the OBS was enough to prevent safe arrival at 3rd.
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Officiating takes more than OJT.
It's not our jobs to invent rulings to fit our personal idea of what should and should not be.
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