I have three playthroughs (X-Box 360) one a stealth archer (by far my favorite, a carry over from Oblivion), a pure 2 handed warrior and a mage. All 3 of them had done the "In my time of need" quest around the same levels, in fact my mage was a bit lower than the other 2 (I know it scales, I'm just pointing out the facts). And in Swindlers Den when you assasinate the guy it was by far easiest with my mage. No idea why, but it was. Stealth archer is still my main char and my fav though.
Appaullo