Age has nothing to do with it, at least that is my opinion. As someone put it to me I like coloring outside of the lines. Embrace your own style, if you dont like your style nothing stands in your way of changing your style. I cannot help but notice that some people (women and men) just give up when they get into our age range. Just my opinion!
When I go to a hair stylist I tell them basically what I want in length. And then I give them my criteria.... I won't comb or brush my hair, I won't blow dry it, I won't color it (I do wash it!).... after I leave the hair stylist it is without adult supervision, so it has to fall into place. I leave the stylist to do what they want. They know what is in style and how to combine it with what looks good on me. If it turns out horrendous, I wouldn't go back; this hasn't happened to me.
Good luck Rachel!
I looked at your pictures, too. Beautiful family!
To the question at hand, I'd say leave it long and curly. You can try a gel or mousse to keep it under control when you wear it down. Layers are good if they're done right; otherwise, your hair will "poof" out.
Find a hairdresser that has experience with curly hair, but don't choose a picture from the hairstyle books; most of those show permed hair, and let me tell you--it's not the same! ( I had curly hair most of my life . . . oh, the stories I could tell! :)