The Missing Mentor boon says that after completing five DC 15 Knowledge (Local) or Diplomacy checks in a settlement of 1,000 people or more (only one attempt per scenario), you get the benefits.
At my location, a question has come up about whether it has to be five different settlements or not. I say no, you just have to succeed at the check five times but they could all be in Magnimar (for example), but others seem to think otherwise.
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I had a blast writing the boon, and I only passingly considered putting in a clause about different settlements. Although my vision when I devised it involved a character wandering around to different settlements, I see nothing in the boon that prohibits one from using the same settlement repeatedly.
The player might get the most role-playing enjoyment out of the boon if he or she uses a different settlement each time, but so long as the player is enjoying the boon, I'm happy.