Hair change?? Thoughts?

I have short, curly-ish, wavy-ish hair. Most of the time I love it. But it mostly has "pizazz" when it's first been cut. Then it rebels. Whisps, unruly curls, triangle-shaped hair (out at the sides, flat on top), ARG! I don't have the patience to deal with it every morning, whether that involves curling or flat ironing.

Right now, my hair is about two inches longer than it is in the blonde photo. Yes, that's my real hair. When my hair is shorter, it gets curly naturally. But at the length it is right now, the curls turn into confused waves and my hair just looks all wonky.
I had some fun and decided to see what I'd look like brunette. I think it's kinda cute, but I don't think I have the guts to try dye. I never have. Even a fade out dye (which is the only type I'd consider) I'm worried it won't fade out all the way. I have a professional job and I have to look... well, professional. I can't have wonky "growing it out from the dye, ignore the half-colored hair" hair.

I think I'm too chicken to color.

So, I need a new cut then. I actually kinda like the cut in the brown-hair photo, mostly because it permits for some wave. I have the patience to make my hair look ok, but not the patience to flat iron EVERY SINGLE HAIR perfectly or make sure the curls are just right. Hmm...

Thoughts? I should probably ask my husband too. :)