Anyway my questions are (And I warn you some are a bit retarded, what can I say, I cant draw

):
Pshah, anyone can draw as much as anyone can write. Well, almost.

If the matter is how good or how bad, it's very subective and a lot of parameters are added to the final resolution wether you "can" or "cannot" draw.
In few words, you must ask yourself a couple things, like... doy ou want to learn or be able to "copy" some other artist or style? Or do yo uwant to use your own?
Do you feel more like a crafty, detailed artist or an animator, simple sketches with less lines for the best effect? or, if you dont know how to answer, i guess yo ushould just see where your heart goes

Anyway for the questions.
1: How much time do you reckon you spend on average on a drawing that by your standards you think is good
Well i measure my level of "good" basing on the tiem i spent on the picture. I cna be happy with a 10 minutes scribble, although it happens rarely. But more realistically, i'd say that a good penciled picture with a hint of background, more than one character and maybe soem hard perspective takes me from 6 to 10 hours to pencil in.
The fact is, i dont always completely pencil in a picture, so i can "stop" the pencil work sooner, i'll explain later.
2: How many (if any) times do you retrace over the drawing to get it looking nice.
I do all my retracing in Photoshop using an optical tablet. Usually, when i’m finished with a pencil sketch, i don’t touch it any further, and do all necessary retouching and retracing in digital way.
Depends on the complexity of the picture, but i retrace freehand a couple of times (one for bigger lines, one for more thin details), and then i trace one final time using vectors, so to lay down the inks for the coloring.
3: Do your mistakes bother you or do you continue regardless
They are my hell, and the main reason why i almost stopped drawing. I’m a perfectionist and one simple mistake, if it gets me while i am a bad mood, can bring me to destroy a pic that would be overall good. I just cannot accept them, even though i know they’re unevitable. Sometimes i manage to jsut let the picture alone for a day or so and next day... i hate it even more and i can it

I’m very eas to please, but when it comes to my stuff... :\ but it’s wrong, very wrong.
4: What kind of pencils do you use to draw with e.g. the thickness/hardness of lead
Well i dont give much importance to that. My favourite is mechanical HB 0.5, but i use also mechanical 4H 0.7 for constructions and wodden 2B for some shading and or heavy lines. but 90% is HB.
5: How do you draw circles *Jimmy hides from laughter*
I stay as light as i can on the pencil (better if it is a 2H or more) and do many quick circles without ever lifting the pencil from the sheet. after 6-10 circles, the “interpolation” of all those lines produces a fairly good circle, that i can trace with a bit more heavy hand.
mostly though it’s a matter of practice. when i’m bored or waiting for inspiration for a pic i just draw circles all over a scrap sheet. After years of drawing, sometimes i can even do a good circle in just two passes. Ah, if only the Simpsons were just circles

[rant] Ive recently started drawing Simpsons again and every time I start a new drawing, I either make mistakes or I draw something that doesn't look right to me or I get all the sizes wrong with the construction lines/shapes and circles give me nightmares. I can't draw Simpsons with open mouths, and as always Lisa's hair is so annoying.
if you want to use construction, then start from the bases and draw EVERY construction line that you can use. compare lenghts, draw skeletons, draw circles for everycing, cylinder for arms and so on. The picture will be incredibly crowded and possibly impossible to understand what’s going on, but with time and practice, you will be needing less and less “construction aides”, and in the end you’ll just use a couple or three plus a couple of lines for movement.
Sizes wrong, it’s a matter of learning, don’t be afraid to learn “dissecting” other artist’s picture. find one that comes close to your idea of good proportions, or better, an official one. printi it, or open it up in photoshop, and try to guess the construction lines drawing them over the character. then take another sheet and draw construction first, trying to replicate the character.
Choose simple poses at first, characters standing and so on. Don’t get perspective involved.
The mouths are easy, once you’ve learned to think about them in 3D, they give sense of depth to the entire head: evne here i suggest you to look at a lot of official pics and see how it goes.
Lisa’s hair is an acquired taste

i made a tutorial once about it, but it was quite complex.
Each time I rub out the paper slowly starts to become coarse and eventually rips and Im wondering if this is just my lack of understanding of all the angles and proportions of the characters, or if everyone makes these mistakes and re traces over them on a new sheet of paper to get them right or if I need a new eraser

It’s a bit of everything. Kneadable easers are good to clean out light sketches, but get good hardy white eraser for the more “rubbery” pencil. Avoid at al lcosts to rub the sheet with the side of your hand... the lightest sweat can make the pencil humid and hell to erase, when you won’t smudge it all over.
As for retracing, the method of transparent sheet is good, but i prefer to do it with optical tablet. When imho a paper sketch reaches the level where i did everything and any more line-erasing would make it more messy, i stop, scan, and work on it digitally.
Of course you need an optic tablet for this. They’re not too expensive anymore and if you really want to learn to draw imo it’s a very handy tool. If you want to get one, get Wacom, dont bother with cheaper brands, they usually have poor sensibility and they need batteries that increase the weight and off balanceness of the pencil.
And I usually end up giving up and scrapping my drawings... Maybe im just not cut out to draw The Simpsons

... [/rant]
Don’t throw them away.. put them away. You never know

Any answer is appreciated as are little tutorials/helpful links. Thanks for reading this
Can’t search for any at the moment, but when i’ll be home i’ll ee what i can dig up.
Practice, practice!