My hair had black perminate color on it and it had got ot a nice white blonde (some parts were more dark but for the most part it was super light. Of course now I have bright colors on it so you cant tell. But anyhow you are going to have to expect some damage....But it can be minimal. I have gone to places before to have it done and seriously they pussyfoot around so that you have to "come back" and they get more $...at least that is what I have found in my past. Anyhow this last time I had my friend help me with it (you really shouldn't do bleach yourself unless it is just in front) Anyhow we used the Clairol's born blonde and the Clairol's 7th stage (we just got it at the local beauty supply) These are made to get dark brown or black hair blonde. And then you want to put a toner on as well....a violet if it is yellowy or a blue if it is orangy.
Of course just as a disclamer you probably wont get the "right" lightness the first time...unless you want short hair
Anyhow you just have to be super nice to you hair after at least for the first few days till the PH gets back to normal.
For shampoos I have used the pricey stuff and the cheepy stuff and what i have found to be the best bet for my $ is Suave (they have a PH balancing shampoo/conditioner) and then I used the Aussie 3 minute miracle. And I try to wash my hair only every other day at least till it gets simi normal.
As far as if it will look like a wig with tan skin...I doubt it...I am actually tan and it looked fine...but then again I live in So Cal so tan with super blonde hair is the norm
You will feel weird for the first few days though.
I hope this has awnsered some ?'s and again it is just my two cents....