On youtube there is a huge amount of (digital)painting and drawing tutorials. To collect the cool ones i started a group on youtube: http://www.youtube.com/group/arttutorials

Feel free to add art tutorials you think are cool to this group!

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Unfortionately I don't know that much programs (Mac user).
For your gif-problem; in PS, have you tried to switch the image from bitmap to rgb-modus first? In rgb scaling will go smoothly, in bitmap it looks disastrous..

I do not exactly know what youtube demands from your video files but i think animated gif is not the way to go to post something on that site. On this page they explain more what to do with your files: http://www.youtube.com/t/howto_makevideo

I have never uploaded anything to youtube myself i just started the group to collect cool tutorials that i spot on that site..