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Just thought I'd chip in and say I actually prefer HoMM2 over HoMM3. I know not many people agree with me, but there it is.
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El_Caz: I'm trying to broaden my horizons and play other genres besides RPGs, RTS's and FPS's. I was wondering if I should give turn based strategy games a shot, though the sheer complexity of some of these games seems daunting at first and usually makes me put them off once I start screwing up and making too many mistakes that kill my fun.

Strategy games I've played and liked:

Warcraft 2, Warcraft 3, Starcraft, Warhammer 40000 Dawn of War Dark Crusade, Battle for Middle earth, original war and the usual standard RTS fanfare that doesn't have trading, diplomacy, 4X anything and consists of mostly building an army and managing them into victory, mostly by sending them to kill units they're string against and avoid their counters. I've never Played any of the Civilization games and did play Age of Mythology but didn't find it overly fun.

Previous turn based strategy experiences:

Silent Storm demo, which i liked but never bought. Age of Magic demo (liked the combat some, got lost with some of the rest), Disciples demo (quickly uninstalled it, didn't know what i was doing).

I look at the gameplay of some of these on youtube and they seem boring, mostly because they're not entertaining visually. However, I like chess and strategy and this is what's making me try and dip my toes on the genre. I was wondering if you could recommend my first experience on it. Don't go for the difficult ones, more designed for people who've had an experience with previous TBS games. I'd fare much better with one that has manageable trading or diplomacy, maybe not that many options or not too confusing.

I know HoMM 3 is highly recommended (I also enjoy good stories) but i'm not so sure if it'd make a decent first time experience. There's plenty of TBS games on GOG, so maybe you could toss up a few pointers, pros and cons on some of them.

Thanks in advance!
It just blows my mind when I hear that there is a PC gaming enthusiast that hasn't played a Civilization game.
In my opinion, Civilization 5 is the best strategy game that has ever come out for someone new to turn based strategy. It's got the best interface ever, so it doesn't have a complex feel to it at all. Then there are the advisors that can be turned on to pop up and explain every single aspect of the game, in simple to understand dialogue ,as you are playing the game. After about 10 turns, you know everything you need to know to play the game. It's a complex game, but it isn't a complicated game at all. You can actually beat the game on its 2 easiest difficulties without really ever even getting into the deeper aspects of the game. Just build stuff and go, and you will soon rule the world.
After a while, you'll be ready for a bigger challenge where every decision can affect your ability to pull out a win over the course of the game.
It's the best strategy game series on the PC, and it's the most addictive game ever made...EVER!!!
You should buy it. You can thank me later.

On GOG.com, though, HOMM 3 is probably the best turn-based game available.
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El_Caz: How much more/least complex is HoMM 2 from HoMM 3? Am I missing something story wise that could ruin one from the other, or are these contained stories with no continuity between each other, simply told in the same world?
First of all don't worry about the story; there's kind of one there in the campaigns, but no one plays these games for the stories. As for complexity, the mechanics between the two games are very similar, with HOMM3 just having a few refinements over HOMM2.