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You made too much progress and are doing excellent... The game is showing it's indignation by not letting the wandering merchant spawn. I've had this happen to be before. Everything was going great, but no merchant, for days... This has happened to me 3 separate playthroughs... I don't think it has anything to do with the way you've built your rooms.
Also, I don't think he can arrive at a settlement if you are there. Or if you are fighting a boss etc.