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I screwed myself in Oblivion, ignoring the main quest too long. The allies that are supposed to help you don't level up, so they end up dead in 2 seconds, leaving you to face impossible odds. Luckily you could reduce the difficulty.

Skyrim initially became a bit harder then laughably easy as a destruction mage. I did go through with enchanting, using smithing to make stuff to enchant. After a while I had 100% mana reduction for destruction magic and access to the highest level area of effect spells. Just spam those as fast as you can click the mouse button...

I like Dark souls' leveling system (for PvE, don't care about PvP) Good balance between upgrading stats and upgrading gear.