I like to cut my own hair. I also cut other people's hair. I used to dye my hair, but now I get it dyed professionally.
Anyway, I've done the bleach + color thing before (red, purple, variations on that theme). It's pretty straight-forward, but especially if you have dark hair naturally, those bleach products you buy at the store will really damage it. Mine felt like plastic. If I were going that route again, I'd get the bleaching done professionally by a stylist I trusted and do the rest myself. Big difference in price, but it would be worth it to me because the bleached hair doesn't recover; you just have to wait for it to grow out.