Master of Magic, I'd say, every once in a while it happened to come to a dead-end in a savegame where the game just crashed, be it through a computer opponent casting Armageddon spell, or me casting Chaos Channels on a unit. That was with it's latest official version, still happens once in while though with an unofficial Insecticide patch.
Ultima 9 might even be called an "unfinished game" actually, as it not only produces numerous bugs with it's latest official patch (and even with the necessary unofficial fan-made patch), but also couple of things in the game show their rather immature state, like the weird, "cartoonish" style of monsters approaching for example.
One more recent game though, which I tried to get into once, is really hell-bent on annoying bugs - Vampires - The Masquerade: Bloodlines. It even has received it's own unofficial patch made by fans, after all the official patches that came out for it. But when it gets rid (read - makes disappear) of your only picklock early in the game, after you reload a game from an unsuccessful attempt to pick a lock, and when it does so again on another occasion after you restarted the game from scratch - you gotta agree, you can't progress in the game with this.
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