the easiest....prolly Peach and Marth the hardest...prolly Toon Link because of all the +2 textures and the most annoying: Ness, Lucas, Kirby, Jigglypuff because of their FS eyes
depends on the character. doesn't take me too long for a kirby/jiggs texture (about 40-50 minutes) and just a little bit more for others. but if it has a whole bunch of +2 or +1 textures, (like Toon Link) maybe 2 hours or so...