Considering going silver/grey and need some advice!

Hello,

So right now my hair is a medium/light? brown?? with some previous (shitty) ombre that I am slowly trying to cut out. My hair is thin, but I do have a lot of it, the brown is my natural colour, and I haven't dyed my whole head in over two years.

http://imgur.com/rvXY4i4

I was thinking of going silver/grey, and have been for a long while... I have a hair stylist now that I know and trust and she said she would be able to do it in one shot, because my base is light enough....I was just wondering with my type of hair is it even worth it? I know I'm looking at a large amount of damage but would it be manageable if I took care of it?

Suggestions and advice would be greatly appreciated!