Scanned most of this thread.
I have almost shoulder length hair. At age 40 I finally grew it out (it was short short for 20 years), then I bobbed it and now it is a bit longer (I am 47 now). I started with high & low lights, now I get the roots taken care of and high/low lights too as needed. I am really good friends with my professional stylist...and she makes me look great.
My hair is not very carefree, but it is what I want/need right now. I really don't know when I will decide to give it up and go grey. Right now I would say never. I don't think I have a nice natural grey (yet) and still fighting the looks of aging.
I guess if I could not afford it, I would give it up. But it is my splurge and I like what I see in the mirror.

K