whats a game that you got significantly far into, only to realize you were doing something wrong or missing a key feature/ability altogether?
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I don't know if this really counts, but I kind of self sabatoge myself with almost any game that has skill points that aren't easily resettable. I'm so indecisive into what to place them into that I end up holding onto the points without using them. So I miss out on power up skills, spells, all sorts of things depending on the game.
I think the worst game I've ever played regarding skill progression is Oblivion.
Honestly, that game's levelling is completely busted. Basically your class has a couple major and minor skills. You gain skill levels automatically by using them, and when you got enough levels in your class skills, you are supposed to rest and gain a character level.
Almost everything in Oblivion is levelled to match your character's level. Gaining a level only serves three purposes : gaining a very small amount of health, gaining a few points in two stats depending on which skills you've used ... And most of all spawning more, stronger enemies.
Lots of skills in Oblivion are not directly (or absolutely not at all) combat-related. Lots of default classes come with quite a few of them as major or minor skills. And those that don't come with several damage-related and several defence-related skills.
Progressing in non-combat skills, or in too many at once in a "master of none" fashion, will make your game impossible. "Playing well" requires knowing and exploiting this by blocking your level up until you've maxed the right skill. Or even having some of your favourite skills not class skills at all.
This is really not my idea of fun character progression.
And you can make Acrobatics a class skill for super fuck you hard mode. I didn't know this as a 13 year old playing Oblivion, and I thought "levels good" and wondered why I couldn't get into the game for years until I learned about this little "quirk" of the leveling system.
Oh yeah, acrobatics and athletics, the two skills that go up every time you jump and run. Good ways to fuck your progression both.
Also the social skills, Mercantile and Speechcraft.