How to get the hair I want?

I have short-ish hair. I got it extremely short in back, and it angled to just above my shoulders in front. I Demi-permanent dyed my hair to an orangey-red color twice, so it's not damaged, except that I straighten it everyday. My hair can get greasy if I use conditioner so I don't use it that often? But anyways- I really would like to get my hair cut to a scene style, an my hair has grown out a little but its still short in back and just past my shoulders in front, and the color has worn out so it's a light orangey, light brownish color. I would like to bleach my hair on top with a darker color like a very dark brown on the bottom, but I'm wondering how that will look ? And if I do that, are there any precautions I should take before getting my hair dyed/bleached and how to take care of it afterwards? And i would get this done professionally not at home :) thanks and sorry it's so long :\