
TheFinish |
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As there are some situatoins where you can get a skill rank in the same skill during character creation I'm wondering if that means you have to choose different skills each or if taking the same skill twice means you become expert in it?
No, all the Ancestry Feats/Backgrounds are specific in saying you are "Trained in X"; and the Classes can only ever get you Trained, since:
"Additionally, this section indicates the number of skills in which your character is trained. When you choose your character’s class, you also select a number of skills equal to this number; your character gains the trained proficiency rank in those skills."
So no stacking Class with Background/Ancestry to get Expert.

DM Ducky |
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There is the Laborer background, which gives you the Robust Recovery Skill Feat, which has as a Pre-requisite Expert in Medicine. So if your GM rules that you have to have the skill to qualify for the skill feat, you can argue that this means you can have Expert in Medicine.
This is absolutely not how ignoring pre-reqs work. You sound like the guy who argued that because he took a Shoanti ancestry trait using Adopted in 1e, which required you to be 8+ feet, he could have an 8 foot halfling. If something gives you a feat or ability without needing the pre-req ability, you don't also gain the pre-req.