Rather than thinking "automatic award", the FED SB rule is written as...
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a. If the obstructed runner is put out prior to reaching the base that would have been reached had there not been obstruction, a dead ball is called and the obstructed runner and each other runner affected by the obstruction will be awarded the base or bases which would have been reached, in the umpire's judgment, had there not been obstruction. An obstructed runner may not be called out between the two bases where she was obstructed.
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If you think about that, it should answer your questions.
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1. R1 rounds 2nd and is obstructed by F6. In the opinion of the umpire she was not trying to go to 3rd base.
2. Same as 1 but she "maybe" could have gotten safely to 3rd base.
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Doesn't matter what she was trying to do - matters what the umpire judges would have happened.
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Does intent of the runner or likelihood of success matter?
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Once again, intent isn't really the question (but it may help shape the judgement)
The whole idea behind the obstruction is not to penalize, but to make things end up they way they would have.
HOWEVER there is one more important part of the ruling and that is...
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An obstructed
runner may not be called out between the two bases where she was
obstructed.
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So, for instance the runner is rounding 2nd (but in the umpires judgement she would not have made it safely to 3rd) and is obstructed by F6, then tagged out (whether she was continuing to 3rd or retreating to 2nd).
TIME would be called and the runner would be placed on 2nd....