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GIMP is when I want to use brushes and such and really play with filters.
Paint.net is for my more basic stuff (contrast, saturation, etc.). Plus the clouds filter on Paint.net is easier and better than on GIMP, so I use it for that too.
First I had GIMP then..
I had Adobe Photoshop 7 for some while then i've got a new computer, so I checked out the CS4 but too much had changed so i've got the trial version for CS2.. Maybe i'll buy it =D