GameBiz 2 - an interesting (and free, it's worth a Google) game development simulator that's very very heavy on numbers, and bombards you with options. I cannot win that game, no matter what I set the difficulty to.

If you like learning challenges I would suggest Unlimited SaGa for the Playstation 2. The developers released it with a very vague manual and was designed to encourage a bunch of players to analyse and dissect the games mechanics and come online and share their findings.

All the footwork has already been done and can be found at GameFAQs in case you ever need hints.

Sins of a Solar Empire was kind of this way for me. Of course, part of it had to do with me having a hard time keeping focused, but trying to remember how to do stuff was too much for me.

I downloaded the trial version of Evochron: Renegades once. I was wanting to try out a space sim, and that one seemed like it would be interesting. Until I got out of the tutorial and tried to remember how to enter a planet's atmosphere without burning up. And trying to remember how to fight without getting killed.

The worst, though, was probably Realms of Arkania. I knew that it would be complicated and hard, but no reviews on this website, no glances at screenshots could prepare me for the horribly complex mess that is that game. It first took me forever to figure out how to create a character, and then I was randomly dropped into a town with no choice but to quit the game and read the ridiculously long and complex PDF manual. After finally figuring it out a little bit, I started playing again, listening to horrible music and staring at old graphics. Getting bored trying figure out what I was supposed to do, I headed out into the wilderness and stopped to rest. I then got attacked...

I'm serious, that game has a stupid battle system. Coming from an unlearned idiot, anyways.

Nethack. Not because of its "interface", but rather because it's unbelievably hard as roguelikes go.

I have limited experience here but a couple of the days on a central Wiki solves most of the problems with an MMO I've found.

In any MMORPG where you play regurlarly with random people you will inevitably come to the conclusion that the game is filled to the birm with complete asshats. It's not the game that's hard, it's just that the level of patience with new players in games like WoW is virtually zero. To top it off many players don't really act that helpful either when a "dumb question" comes along, so you end up being yelled at instead of getting a helping hand.

All in all, MMORPG communities suck.

War in the Pacific.....I'm on my third day of studying the 350-page manual to try to learn this behemoth of a wargame.
I might give up on it.

It is a very hard game, but it is rewarding whenever you reach a new area for the first time, it's rather cool. I say this as someone who has never made it further than the (optional) sokoban stage....

Now that I've reinstalled Ho2 and looked at all of the menus in this game , I'm reminded why I decided to put it off in the first place. Goddamn this game is complicated

uhhh..I think I'll go eat a sandwich and work on my spongebob squarepants netflix backlog instead.

I don't know if anyone mentioned Dwarven Fortress yet, but I believe it has somewhat of a rep for being really, really "deep" (a nice way to say "hard and complicated as hell").

Oh yeah. I was very surprised at myself when I completed it yrs ago (w/a knight character). It almost seems like a stroke of luck that I did!

The hardest of those games were 'Larn' and the original Roguelike, 'Rogue.' Though I'm pretty sure a couple of Angband variants are even tougher than those games, nowadays.

It also took me YEARS to complete Dungeons of Moria. That was my favourite of all Roguelikes.

One game I remember is the Dominions series by Illwinter, which are fantasy strategy games. The interface was pretty obscure in the first couple of games. The interface got better in later games, but it was still hard to get a handle on the mechanics.

I suppose the biggest difficulty was how all armies required a general. You couldn't just build a stack of units at a province and send them off. You had to send a general to that province, build the stack of units, assign the units to the general, and then send them off. Also, you buy individual soldiers, so it was sometimes hard for me to judge how many soldiers exactly I should build.

You actually beat Nethack?!

I've always been an Angband player myself, and I don't think I've ever gotten past level 15. Not to mention the plethora of Angband variants that always add extra-powered monsters and other crazy stuff.

The interesting thing about roguelikes is that I usually steamroll through everything, and then suddenly hit a brick wall of a monster that causes the "would you like your possessions identified" screen.

Can't disagree with that:)
Actually, you can get used to any game, with enough patience, i think. Even something like Super EF 2000 or Capitalism(Ugh... maybe not this one:). In most cases it's just the interface that puts you off.

I agree with this, but more for the look of the game. I keep trying, but even with tilesets, I can't tell what I'm looking at, i feel stupid because I don't know if I'm running towards a mountain or a town, and I eventually quit.

Yeah man! I even had time to do the knight's subquest! It was awsome.
But I was so lucky, as all the items I wanted, I got. This including the stethescope that told the creatures alignment, hit points, and magic effects!

I never beat the original Hack though, where Nethack spawns from.

Shortly after beating Nethack, my pops bought me my 1st copy of Baldur's Gate II: Shadows of Amn! It all came together like a graduation present for beating Nethack!