Hello I was thinking try out a playthough like this and kida roleplay it a bit but I'm little worried about doing it since it involves some cheating.
As we know that our character was trying to crossed the border when he/she was caugh during the ambush, anyways lets get to my ideal of a ropleplay all tho I don't usally roleplay.
(Character Name) Was visting his/her homeland or just visting skyrim. When they got caught they imperails tooks their gear away and put give them rugs to put on. After the character bindings are cut of the character finds their stuff in a chest which contained. Dedric Bow, good gear haven't decied which gear I will use, Maybe dedaric daggers or ebony then later on i will get the blade of woe and that razer dagger legity. My char would be skilled in archry and sneaking maybe even illsion and would be level 1 or maybe higher but I would hadd like 1000 magika, 1000 stama, 100 hp. Not sure if I would enchanted the gears yet.
I'm just worried about getting bored of hte fact i chetted to get what I have ETC even know its roleplaying.
I did do a playthug to level 41 one leglt then start exploting with that book glitch after and beat the game which i regerted later on.
i think you should just limit your way of playing so that it is harder and more fun. starting with a buff weapon or armor and one shoting stuff is too easy and gets you bored quicker...try doing steel only till level 20 or leather. or steal stuff to survive with no buying things, except for spell books... i dont play pc so i do these kinds of things to keep me in the game longer on the xbox 360. you will find playing on the xbox or ps3 is way more rewarding than pc in alot of ways, for a couple of reasons... Your not tempted to turn on god mode or cheat by adding items by console, or buffing your skill stupidly high so that the game is no longer a challenge and makes you bored way too easy, unless....you get lots of mods...
i love playing on the pc, so i have no problem with people that play on that, but its when they cheat so baadly on the game and complain how boring it is that pisses me off. i would love to play skyrim on the pc, but i'd have to get a new one to do so and i dont have the money. the only reason i would play it on the pc if i could is becuase unlike the xbox, i love mods but not game breaking ones (in other words, i like new content people make for the games) thats why morrowind is my all time favorite elderscrolls game.
im even playing daggerfall too. anyway i hope this helps and im not flaming the pc users, just adding my oppinion..
p.s. if you get to the book quest use it once and let it die in the game so you wont be tempted to loop it to max out.. and yah, i did the same thing just to see what happens, but i dont even touch that character anymore. i actually rp character now on skyrim...

its actually fun and challenging...