
Wogan |

Secret:At 1st level and every two levels higher than 1st (3rd, 5th, 7th, and 9th), the loremaster chooses one secret from Table: Loremaster Secrets. His level plus Intelligence modifier determines which secrets he can choose. He can't choose the same secret twice.
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You are able to choose a Secret from the list given under the PrClass. This list includes Applicable Knowledge and Instant Mastery. Under the descriptions of these Secrets you are than given the option of what this Secret applies to. This means that you are still selecting the Secret "Applicable Knowledge", however it has a specific effect that you can choose after it has been selected.
Taking this into consideration, you are unable to select either of these Secrets multiple times. I understand what your reasoning is, however I am sorry to say that it is not how the rules of the PrClass is written. You do not select the Secret "Applicable Knowledge: Iron Will", you select the Secret "Applicable Knowledge" and than are given the selection of what feat you would like.

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Can a Rogue select Combat Trick many times, thereby making Rogue Talents strictly superior to fighter bonus feats and making talents like Finesse Rogue completely redundant? Same question, same answer.
Since there is an archetype (Swashbuckler) that specifically grants the ability to take Combat Trick twice, Paizo has answered that question.