Planescape
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Eugene
Oregon
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I have heard its good to use only 1 or a few expansions at once, and I would like to get the one that makes the game the hardest to beat.

 
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Nathan Little
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If it is the only expansion you are using, I'd probably go with Dunwich. Nothing good happens there, and if it's the only expansion pack you're using the gates will be more likely to show up there.

Of course, if you're just trying to up the difficulty to nightmarish, just play with heralds.
 
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Will
Argentina
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I recommend the King in Yellow. Used on top of the decks is a killer.

Also if you dare to use Lanius home rules, the base game comes to what it was supposed to be. Pretty hard indeed:

http://www.fantasyflightgames.com/edge_minisite_sec.asp?eidm...
 
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Here is a short overview how I would rate the different expansions in terms of difficulty. I play Arkahm Horror a lot with my girlfriend with each of us playing with only one character. Additionaly, we always use Heralds, the injury and madness cards from Dunwich and the epic battle cards from Kingsport. Plus environment cards are cumulative, if they aren't related to the same realm (urban replaces urban for example, but if weather or mystic shows up, all of them will remain in play).

Curse of the dark pharao
Nice and a good choice to raise the difficulty level in a moderate way. Can be beaten when playing with two players.

King in Yellow
One of my favorite small expansions. It raises the difficulty level to a challenging level, but it can still be beaten with two players.

Black Goat of the Woods
This one is hard. We didn't manage to beat it yet (2-4 players) - all attempts so far were smashed without remorse. Especially when playing with Shub'Niggurath, whose herald is included in the box. But we'll keep on trying.

Dunwich Horror
Nice big box expansion, can be hard to win. But it may occur as well that nothing will happen in Dunwich. And then you're ending up playing the base game with just a bigger board and more cards.

Kingsport Horror
Also pretty hard. The rifts are forcing you to always have a close look on whats going on in Kingsport. The rifts can open very quickly and closing them takes some time. Time in which they keep on spawning monsters and, possibly, doom tokens. Not beaten with two characters yet.


Since I haven't played Innsmouth Horror yet I can't say anything about this expansion.

My recommendations are:
Black Goat of the Woods, if you want to buy a small expansion.
Kingsport Horror, if you want one of the big box expansions.
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David Sleaze
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Hardest Set up that i know is King in Yellow + Dunwich with the King in Yellow Herald... Yellow Signs can realy ruin your Day , espacially if monsters in Dunwich keep running into the Struggles to raise the Terrorlevle and trigger the Herald...
 
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Kris Van Beurden
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Leuven
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Innsmouth by far.

Everything goes as planned, your investigators are in the Outer Worlds carrying enough clues and elder signs and having all equipment to safely seal the last few gates to win, and suddenly, due to some monster surges and seal bounces, the deep ones track fills completely and the GOO awakes out of nowhere!

OR you can go and fill the FBI Track with six clues, and then come 6 clues short for your final seal... (and still get the Deep Ones track filled again).

EDIT: Oh yeah, and combine this with the Mother Hydra and/or Father Dagon heralds ...

Again, Innsmouth by far.
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