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I think we should break-up the Skill masters by level. So, the ones we know now would be for levels 1-20; there'd be new ones for levels 21-30 and so on.

Where should they go?

For Thief, obviously, Capitoline.

What about Herbalist? Healer? Malopath? Warrior? Etc.

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SmartMonsters' Bulletin Boards
Post early, post often.