To Do or not to DO???

I generally consider myself a blessed person when it comes to my hair. I adore my natural color - though, I will not lie - there have been many times when I have fiddled with the notion of going jet black or blonde. It always falls back to 'but, I just love the way my color looks in the sun - and it feels so warm to me.' Then I inevitably chicken out & leave it the deep rich, multi hued chocolate swedish brown that I was born with. Oh, sure, there have been times when I had a streak of blonde (called it my mean streak) and a few times that blonde streak met up with a bottle of Manic Panic in Vampire Red. Then it was a really mean streak.
But, I have been quite lucky that I have a highly talented sister that happens to cut hair.
Now, she just does it when she wants to now. She used to cut full time as a licensed cosmetologist, but now, she's a licensed 'bambulance lady .... EMS, Paramedic .... I really don't know the difference.
My latest cut is something ala Jennifer Aniston. Long, flowing layers that blend into each other.

Jenneyfur did it with a razor - which I gotta say, hurts, but looks kick ass when it's done.
Before that I always just let it grow, and she gave me trims to remove split ends - which I loathe. For years I generally felt that I looked like an out of place flower child that only needed a daisy chain crown to finish off the look. It turns out that when I let my hair grow, it is so dense, and heavy that it looks bone straight. Which is kinda weird, because I have kind of a natural wave to it if I keep it at any reasonable length. This is what my hair looked like for nearly 15 years.

Then, during a moment of irritation with my hair, on a night when my sister happened to be over to my folks' house doing hair cuts, I asked her to cut it. Really cut it. I wanted to try out a pixie cut. She was hesitant at first - and rightfully so, since I had at one point disowned her for trimming off 2 inches more than I had asked. She was nervous, but I insisted. Cut it. And, so, for a year, I kept my hair more to this style:

It was cute. It dried so fast I couldn't hardly believe it. But then, the downside reared it's head. I had to trim it ALL THE TIME or risk looking like the bad hair bag lady. Oh, and I missed the ability to put my hair into dual braids ala Little House on the Prarie. So, it had to go.

I find myself fighting back urges to do something wild to it. Like go blonde, then mulit colored. Or cut it all off again. Or ... who knows what. So, I am looking for suggestions. Please, let me know what I could try. I don't have a recent pic of myself, but I can tell you I have really HIGH cheekbones, a smallish, up turned nose, hooded eyes (brown) and fair eyebrows & skin.

Please help before I do something radical, totally. Like this.