Should I go lighter or darker? (Hair)

http://www.flickr.com/photos/bagley777/8293721206/in/photostream

There’s a recent picture of me. As you can see, I have medium/dark brown hair, blue eyes, and SUPER pale skin. I’m planning on dying my hair for the first time ever, but I don’t know if I should go lighter or darker. Not blonde or black, but a dark or light brown. Either way, I’d include highlights and lowlights so it wouldn’t be so flat. :)

Darker: Pros – Might make my eyes pop (I’ve always thought dark hair/blue eye looked pretty!) Don’t have to worry too much about roots, won’t damage my hair as much. Cons – Might make me look really flushed (because of my pale skin)
Lighter: Pros – Safer, would make me look “nicer” (I read that somewhere), might go better with my skin. Cons – More high maintenance, Might damage my hair, no “pop” to it.

I’m also looking for style suggestions, I’ve had this hairstyle for about four-five years now…I’m ready for something new! Bangs, layers? Short, long? What do you think? Thanks!

ADDITIONAL DETAILS: (Don’t have to read! Just some things that might be helpful, if you know a lot about this stuff.)
I have an oval face.
I normally wear contacts
My hair is naturally wavy, and I almost never style it.
I have a “cool” skin tone
I’m willing to go a lot shorter…but it needs to be passed the face, at least.
My hair is VERY thick
And another question is anyone knows about colors and skin tones, I was thinking about red-ish highlights in my darkish brown hair. Would that work with a “cool” skin tone?

I just asked like 3 questions :/ Sorry! I’m new, and curious. If you can answer any one, it would be much appreciated. :)