I'll set myself up for drama right off the top by admitting that Skyrim is the first TES game or single player game of it's type I've ever played. I've played lots of MMO's which are only vaguely role playing games, even on RP servers. I'm also not as young as I look and played a number of the good old fashioned RPG's back in the days when they still required hours of negotiation, dice, paper and pencils and stacks of hardbound books on every flat surface in the room.

I'm utterly baffled by the use of "on this play through I'm going to be a good guy" and "I decided I'd play a bad guy and be a thief" and the thousands of other sort of... box shaped contrivances I've seen people admit to placing on their characters.

In my mind that box around the character is actually contradictory to role playing. My thief IS my good guy! She wasn't born that way, either... it just sorta happened that way and she seems to dig it, so who am I to argue? Her allignment is certainly not lawful anything, she's definately not even really "good" by the truest definitions of the word... and she's still on a very altruistic and generally mainstream questline through the game. It's my spellsword the world needs to watch out for, doesn't carry a weapon, wears only heavy armor and has his eyes set on a particularly lovely daedric set. A knight and not a good one. He started out pretty good, headed for a life retired at the top of those 7000 steps, married to a girl down in Ivarstead. And then... well, power corrupts and absolute power corrupts absolutely.

My point is that if you're really good at role play then boxes are for babies and putting yourself in the place of having to really decide "would this character take this opportunity or would he/she walk away?" and then following that with the question "how does this change this character and their views?" is the only way to play.

Am I being a purist or is my own personal chaotic neutral allignment showing through?

While I applaud your philosophies regarding roleplay it's still up to each player to choose how they play the game in order to enjoy it.
Though I strongly recommend everyone to try not to put each character in the above mentioned box, at least once

It's part roleplay I think but also part wanting to see what a certain playstyle has to offer. I do create characters from the get go with a certain morality but it's not an unbroken bound but it is a guideline. That morality is totally seperated by class/playstyle. My barbarian murders most elves he sees but he's not evil, he just really hates elves in general My Imperial soldier was more or less good because he served the empire and what it stands for, upholds it laws etc. On the other hand he freely kills rebels, daedric worshippers and other 'scum'.

There games where I play clean good and bad guys, Mass Effect come to mind. This is because both paths can give different experiences that really are different. Skyrim misses those so there is rarely any insentive to play things a way just to see content. I rather not play certain content because it doens't fit my character. My thief killed but the DB liked it way to much for her liking so she dropped out.

i usually chose my toons to be in a pre set class i whant to play, after i start the game they gain a life of theyr own and they are either mixed duvious toons or malicious mercs or what ever they grow in to

I wish I knew how to roleplay but whenever I try to start it just turns me right off the game i'm playing for some reason

Skyrim doesn't really do allignment... there's not a set path one can call "good" and another you can call "evil". The closest thing to it is how they deal with the Dark Brotherhood, but even that is bendable.

You can go a step further and ask what is good and evil? Who or what determines that and how do you know you're playing one side and not the other?

This is why I usually play my character to be impartial and absent from most people's affairs. The less involvement my character has in assisting other people, the less likely he is to fall into the trap of being a hero or an instigator.

my boyfriend did point out that there are a great many games that choosing a class ie: thief will set your allignment, or cause you to deviate from the one you've chosen and in my own example I do have to admit that there are some activities that are outside of a given character's role. I just don't believe "good" immediately sets defined "rules" on a character.

I think my difficulty comes from the very many posts of "I'm going to play a good guy so now I can't do... [insert quest chain here] because it's all evil" or "my thief is supposed to be bad and [insert chain here] is just too rightious..." to which i have to ask why did you undertake it from the start?

Is my thief challenged by a Thieves Guild that does not take care of older or "retired" thieves in other cities? Yes. She would "hire" Silda the Unseen in Windhelm to guard her house and have a warm place to sleep forever out of a sense of family and loyalty that goes far beyond the game... would that same character be saddened to collect on shopkeeper because he hasn't paid his "protection" money to the guild? Nope. Business isn't personal. Do I personally get a kick out of trying to find new spots for her to loot on bedlam jobs? Youbetcha. She's still a bleeding heart and gives money to vagrants and is conflicted because I found that Nocturnal and Kynareth really aren't at cross purposes, if you examine them and so the Way of the Voice and being a really good thief seem to both flow naturally for her. Would she split you open from behind in the dark because you dared interrupt her looting your home? Nope. I believe she'd be bothered by that a real lot and would be more likely to book bootie right out of your home and come back later instead.

I have some characters that are just what they are, I have a couple that were simply tests to see if I really "got" the mechanics and understood the class I was playing and others with a clear RP set from the start... I like going back and forth between them because it's restful.

I love that so many of you are able to define the answer for me, and I'm actually glad to say I'm learning a lot from what's said here and privately.