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In the Core rules, three backgrounds give you the Assurance skill feat: Farmer, Nomad, and Scholar. The first two specify the skill you gain Assurance in (Athletics and Survival, respectively). Scholar specifies that you're trained in your choice of the four magical skills, and that you "gain the Assurance skill feat in your chosen skill."
If a Bard takes the Scholar background, e.g., they get the Occultism skill from their class. Per the rules, then, they can take a skill of their choice from their background. Do they gain the Assurance skill feat in that skill, even if it's not one of the four skills listed in the Scholar background?
I'm assuming not, since choosing a background comes before choosing a class in the formal character generation process. That is, the not-yet-a-bard takes Occultism from the Scholar background first, gets Assurance with that skill, and then gets their choice of a skill to replace Occultism with when they pick their class.
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The full sentence reads
You're trained in your choice of the Arcana, Nature, Occultism, or Religion skill, and gain the Assurance skill feat in your chosen skill.
You can't apply the assurance skill feat to a skill that isn't one of those choices. The antecedent to "chosen" in that sentence is "your choice of". It's not talking about some other skill you might select at some other point in the process.
And yes, during character creation, if you would be trained in the same skill twice, you can select a different skill for that training.
If your class would make you trained in a skill you are already trained in (typically from your background), you can select another skill to be trained in.