Wow! Thank you all for all the feedback, it's been very helpful. To respond to some of your posts, then at the end, I'll share what I've decided.
Ok, girl.. Your a survivor, it sounds like you've been through a lot, and you came out on top. Big hugs to you.
I'm 41, I don't have grey hair.. Yet, anyway. But I have decided to stop bleaching and let my natural dark blonde hair grow out. Like you, I'm currently rocking an asymmetrical bob throughout this transition. I say go for it! I feel like I've reached a point in my life, where I'm over "conforming to that pressure". This is me, take it or leave it.
And, it's just hair, you've been through worse and it grew back. I say give it a whirl, if you try it and you hate it, you can always go back to dying it again. But I think you just mind find, that your comfortable with your dents and scratches, and love it.
Thanks, I have been through a heck of a lot. It's still a daily struggle. I am used to my dents and scratches, just a little nervous about adding grey hair over all the dents and scratches. Lol. You wrote how I feel, it is just hair, and I've been through worse and it has grown back. My hair grows pretty quickly.
Coloring my hair is something that I only started over the last year and a half or so and I just turned 39. I have grays at my crown and my hair dresser does highlights in light blonde so that they blend rather than trying to cover them. I have naturally caramel colored brown hair so I really like the look and I can usually get 6 months or so out of one appointment.
I agree with the other poster who said try it out, if you don't like it you can always dye it. I would just add that if this is the one way that you pamper yourself please replace it with something so that you don't feel as though you are neglecting yourself. Whenever I make a drastic hair change I like to buy a new brush or styling product to go along with it.
Oh, I like that,,, and completely agree. Find something for you, maybe a massage, manicure, pedicure, new shoes, new purse, take an art class, something. It's ok to be selfish sometimes.
This is excellent advice! And really hit the target. Being on disability, I cannot spend a lot on myself, and I do get my hair done, but I never go anywhere. If I didn't dye my hair, it would free up money for me to go to the movies more often, which I would like, and it would get me out of the house, which I really need to do.
I'm 50, and I've been letting my colored hair grow out for a year. I've always worn an inverted bob, but just got mine cut today into an edgy pixie. When all the extra hair came off, i discovered that my hair is a bright silver, with white highlights, lol. I love it. I go to a salon where the stylists are a bunch of hip millennials who wear combat boots and have tattoos. My girl told me I would be crazy to color it because it was "on trend". I thought that was so funny, because at 50, I'm finally "on trend"
It is funny to see all these younger people with silvery grey hair that's so trendy!
I'm 40 and I have more than a few grey hairs. Luckily, it totally blends in with my hair but I won't colour it when it gets more noticeable. I'm like you, some (ok most) days I feel like I'm 90 so hair colour is the least of my worries.
I know you understand.

Chronic illness and or chronic pain, is unbelievably difficult.
Whatever makes you feel best is foremost. I'm 58 and I've decided to quit and let the grey come out. I am about 90% at this point and I have a pixie cut. The only thing I am going to do is add back in the purple streaks I had earlier this year. During the summer they faded out from sun and chlorine. I like having some fun with my hair and I have had so many positive comments about the purple. The main thing to remember is that if you don't like it, you can change it.
That's awesome. I would totally think about adding in a little pop of color. Purple, or maybe blue.
I think gray hair is classy as women age. It must be maintained of course. But I have known several women in professional positions who let their hair go gray naturally. I think it is a very graceful way to age.
Yes, I would still get it cut regularly. Seems like people do not age gracefully these days. Surgeries, face lifts, Botox..... I feel like it's this unhealthy obsession with looking as young as possible.
Call me vain, but I'm not ready and I may never be. My DMom had her hair coloured up until she was transferred to a locked-down dementia care facility at age 97. We would have kept having it done for her there too but the service wasn't offered. She had a very difficult time recognizing herself in the mirror as it rapidly progressed to snow-white.
OP, I feel you about the cost, especially if you're trying to maintain roots on a dark shade. I'm in that same boat and have to colour every 3 weeks; 4 and I'm getting "skunky" which I'm very self-conscious about.
My vote is that you learn to DIY (box colour as the stylists call it). Besides the very occasional set of foils, I haven't paid a stylist to colour mine since I can't remember when. Lots of products are easy to use and give good results, especially if you're using your natural colour. I agree with cantw8 that it really doesn't sound like you're ready to let it go yet.
I cannot really do it by myself anymore, I used to be able to, years ago. Due to radiation damage, I have really bad peripheral neuropathy in my hands and arms, and I cannot really get my arms up, especially my right (dominant hand) up to my head. That's also why I had to get my hair cut super short, I just cannot maintain long hair anymore. Too hard for me to wash, brush and dry! I also don't really have anyone to help me do it.
I would only go gray if you have beautiful gray hair. Some men and women do. Most do not. In my experience, those women that were once fairly light blondes end up having pretty nice gray hair. If you were a mousy brown or dishwater blonde, you will probably end of with that awful color of gray. No one in my family has nice gray hair so everyone colored up till the end! If it's the bad gray, your skin will look very sallow. A good haircut will help that as well as a well made up face, but you want to opt out of the makeup.
I vote that you should color your hair.
I think I will have nice grey. My hair was very dark brown. Also, my gram never colored her hair, and she was grey in her 40's, and it looked good.
I never wore much make up, to be honest. Very rarely, like a few times a year. Now, with my hands being numb and weak, and not being able to see without glasses, it's just too hard to put on.
I quit coloring mine a couple years ago. I'm gonna be 50 in a couple months and I have quite a bit of gray, but I'm okay with it being natural and not having to be a slave to my hair anymore.
It does feel that way, like I'm a slave to it. Also, if I let it go my natural color, I'd be able to style it in different ways, instead of be locked into my one style, because I'm always trying to hide my roots that grow in all too quickly, my hair grows so fast.
I go to my salon every 6 weeks without fail. Yes it is expensive but I am worth it, lol.
I am not grey, older than you, AND dealing with cancer treatment swelling.... so there.
Bottom line if you are going to grey, you still need to go to the salon to keep it looking fresh.
Yes, I would still keep it styled and cut. In fact, I would have more styling options if I let it go grey. Good luck with your treatments.
I have decided that I think I'm going to grow it out, and get it cut, and then sit with it a bit and see what I think. I can always dye it again. I know I'm completely sick of having to dye it, and I don't know if I will like it grey or not, but there's only one way to find out.
It would be nice to not have to spend so much on my hair, and free that money up to go see a movie a couple of times a month. Or for something else that will get me out of the house.
Thanks again for all your thoughts!