With Elder Scrolls games I usually play my first character by the book, doing the main quest and whatever side quests I run into as I level up to God mode level of skills and gear. After that I like to go back and role play low powered characters. The hedge mage/poacher/street punk that do the apprentice level rat hunts.
For this I found that Morrowind was the best simply because of the sheer number of quests you could play and the little tricks in the gameplay mechanics like low powered one mana point spells you could custom make. Oblivion the gameplay wasn't as favourable but, because of the levelled monsters, there was a huge number of quests and dungeons you could explore as a low level character.
In Skyrim they added a lot of flavour options for a peasant play through like gathering crops and chopping firewood to earn money but, this may just be a personal experience thing, it seems to me all the quests start out at the journeyman rather than apprentice level if you get my drift. You get sent out, right from the start, hunting bandits, undead and even dragons rather than low powered critters. From there you level up pretty quickly and I never really could capture the feel of some young kid with a sling shot and rusty pocket knife trying to get his start in the world.
I was just wondering, am I missing something here or is this a common experience for everyone else?