Can I housefriend a guild, give them permissions, then housefriend a player from that same guild and give the player different permissions? And which set of permissions will the player have?

Yes. You can give the guild one set of permissions and a player from that guild an entirely different set of permissions. Individual housefriend permissions will always override guild housefriend permissions. For example, Guild A is set as Visitor with one set of permissions. Player B, a member of Guild A, is set to Ally. Player B will have Ally permissions, while the rest of his guild will have Visitor permissions.

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