This is precisely why I prefer to use paper for the drawing portion of my art. 
I love the graphite, Ticonderoga #2, but I'm so heavy handed that occasionally it gets out of hand, with painter, I can go crazy, and erase and smudge and draw again without killing even the thickest paper! But I jump back and forth. Being able to resize the canvas after you realized that you're going to chop off some feet is also a huge bonus.
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It's easy enough to use the alt+spacebar to rotate in painter, I wish the rotate in photoshop was as good, but in photoshop, you're actually rotating the image which depending on the size can take some time to process. But I like that idea!
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Alt+Space FTW!
I never work on my paintings square with the world. I've not played in Photoshop much in part because the rotating it is so important to me, and the pixels would distort with each canvas rotation if I did.
If you could get your brain to process the change ... you could just turn the tablet. But that would take some training too.
Char Site | My DeviantArt
Global=@Thornster
I agree, Alex, being able to resize the canvas, move the image on the layer, rotate something that's off, are all wonderful tools that digital drawing can bring you.
Also, I highly recommend an Intuos tablet with a large size (mine is 9 x 12) because they have have 1024 levels of pressure and that's very important for any deeply involved digital artwork.
As for the learning curve, in my experience, the hardest learning curve to over come is the fear of using the tablet. The best thing to do is to jump in with drawing and/or painting. It's like any medium, it takes getting used to.
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Alt+Space FTW!
I never work on my paintings square with the world. I've not played in Photoshop much in part because the rotating it is so important to me, and the pixels would distort with each canvas rotation if I did.
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Seriously!! I so didn't know about that! MY God, this will make things so much easer for me! Hell, I would end up just rotating the canvas like 90 degrees, wait for all layers to rotate, then make my few marks in that direction, rotate back 90... god, this will be much easer (I was also afraid that it would distort the pixels my self).
As for learning curves and all that, i actually find that Graphire has a much larger learning curve the intuose. It really didn't take me any time to get the hang on my intuose (and it has a roughish surface too... not that slick plate that graphires have) however, trying anything on Stars graphire just drives me up the wall.
For me, like others, the hardest part is just not flipping and turning the tablit to get a better drawing angle XD. Now, all of my preliminary sketches and posses are done all digital with my tablet. The fact that i can erase anything, rearrange parts already drawn, etc, make it a very valued time saver in the conceptualizing part of a piece!
From when I first started looking into a tablet, I've been looking at the Intuous. I got confirmation today that I am in the class that I registered for a week or so ago, so I'm hoping the class mixed with my own sketching whenever my hand picks up a pencil will be able to allow me to justify a tablet purchase.
Trying to psyche myself out by getting an expensive toy so I'll be forced to use it doesn't work. So, I'm trying the alternate approach of telling myself if I can get good enough that I can justify its use to myself, then I'll spring for one.
I think that the class I'm taking will help some, but I think I also want to take a figure drawing class.
If I can force myself to pick up my sketchbook at least once a day, hopefully more, I think I'll soon start to see improvement and then be able to reward myself with a new tablet.
Thanks again for all the suggestions and advice. The support here is very helpful and it helps me to keep on going. Now I just need to draw something I'm happy with so I can post it here.
Cosmic
It's easy enough to use the alt+spacebar to rotate in painter, I wish the rotate in photoshop was as good, but in photoshop, you're actually rotating the image which depending on the size can take some time to process. But I like that idea!