So a search of this forum turns up a grand total of only 8 topics that even MENTION Daoloth, and none seem to be exclusively focused on his (its? I'm new to this whole Lovecraftian horror thing) crazy power. I think he / it deserves

I was playing a game by myself on Vassal, controlling 6 investigators. I ended the first day with no monsters, three monster slots, and no Other Worlds. I don't even remember if there were Other World rewards on the Adventures in play, because I don't think I was all that concerned - I had THREE slots open! I think I figured I was FINE! The lingering effect of the initial Mythos card was "a monster appears." I went into midnight knowing that I could handle that, and surely no new Mythos card would give me three monsters...

But then I drew a Mythos Insight card: either discard an Other World adventure or three monsters appear. Eep. Well, no Other World adventures, so let's put out those monsters. Okay, I'm going to have to lose one investigator, that's no problem, there's plenty left...wait...a doom token puts out a monster...which means another investigator is getting devoured...which means another doom token...another monster...another devoured investigator...another doom token...another monster...A FOURTH DEVOURED INVESTIGATOR.

It was in that moment that I truly understood the insanity that is Daoloth. Four monsters at one midnight = 4 devoured investigators.

A thought on that - could I just devour each new investigator as it's put into play when I know I'm losing four in a row, or am I supposed to lose four investigators that were already in the game at the start of the effect? I think it hurts more if you have to lose existing investigators - that is, four out of the original six - because you lose trophies and items that they've collected. (Although I guess if any weren't doing so hot, a replacement investigator with those starting items might be just what the doctor ordered.) How do you play this? (Slash am I making my question clear?)

Yeah, Daoloth is a monster. His ability doesn't seem too terrible until you realize that he's effectively a house of cards.

I'm thinking that the doom token and the replacement investigator are simultaneous, so you can choose the order they get resolved. In this case, as you indicate, it would be more beneficial to draw the replacement before adding the doom token that devours the next guy.