Illuminous all those against reasons are the ones I have tackled. I found Anne Kraemer’s findings incredibly helpful on the ‘will it make me look old/will I look less attractive’ front. She carried out various experiments as part of her process and the findings were surprising.
One thing that she noted is that she took more care over the appearance once she transitioned. She had more money to and noticed she hadn’t updated her style or looked after her health because dyeing her hair, she felt at the time, offset all these things. She had a reality check when seeing a picture with her hair dyed and she noticed how artificial it looked. She didn’t look younger for all the time and effort that was going into dyeing her hair and was dissatisfied with the colour when she had dyed it.
My impression about the younger generation is that they think grey hair is ‘cool’. They have grown up with it being fashionable and I have heard quite a few women comment that once they have gone natural they are complimented on their hair in a way they never were when they dyed it.
What I will say is your list of advantages far outweigh the negatives. The thing that struck me the most was your comment on having an itchy scalp after dyeing -it can be a sign you have started to develop an allergy to the dye. That is quite worrying and obviously a major consideration.
The way I see it is all the money spent on dye can be reassigned to nice clothes and make-up and feeling good in that way and if you really don’t like it you can just dye it again. However, once women have tasted the freedom from the tyranny of the tint very few do return. Most cases I have read -the women say they can’t believe they were covering up the silver treasure that lay beneath.
One thing which might be helpful whilst you explore if this is right for you is to gather some pictures of grey hairstyles you like and read forums especially supportive of grey hair. It can help visually breakdown preconceptions and fears about what going grey means or alternatively establish if you are just not comfortable/ready yet. It can also help you think about how you want to transition if you decide the time is right for you.
It can be a very confronting and yet exciting process is my take on it.
Reading your list it sounds like you are more than ready but are worried about how others will view you. Have you had a chat to your DH? He might surprise you 🙂