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To unlock the hobo go start a single player game with one character, a huntsman, because you can run away easier. Earn exactly 40 gold. Click next turn while the world burns around you. If you die of chaos then start a new game and do it again. If you see a purple ? then run from every fight on the way there and give them the 40 gold. that's it. That's the best way as far as I can tell.
I haven't unlocked any further characters so I don't know if they require single player also.
Good luck.
-For the Monk > Find the Yeti snow cave in the Frost Campaign, you got to make a sucesfull roll to save him after fighting the Yeti
-For the Treasure Hunter > You got to rescued him from the Whale's Belly in the Into the Deep campaign