Advice?

I need some advice about my current hair color situation.

My hair is naturally an ashy blondish-brown that tends to look gray or non-color. I've been getting blonde highlights since I was thirteen, and when I was seventeen I dyed it bright red. It faded to an awful pale, orangy blonde, and my hairdresser gave me blonde highlights to blend the terrible color with my roots. That was in August.  In October, I dyed it a medium golden brown, which quickly faded to a light brownish-red.  Then in January I dyed it to a very dark brown. Horrifyingly, the bottom of my hair was black, so I had to get it cut. Since then, it has faded to a medium reddish-brown, and I have about an inch and a half of grayish/non-color hair roots.

Now I have a dilemma -- I don't think the dark hair looks very good with my complexion and the roots are a disaster. I would really like to dye it a strawberry blonde, which would go much better with my skin, but I'm very hesitant to use bleach or have it stripped. I have 3a curls and I'm afraid that I would be left with a dry, frizzy mess. And what color would my hair turn if I did strip it?

Basically, I need help deciding if I should just grow my hair out despite the very light roots, or try to take care of it chemically.

Help!