Ok, here's my honest (general) opinion.
Gray can look very classy and wonderful, but it does age you. So it really just depends on how important it is to maintain an image close to your age. For example, I work with someone who is 33 and has a full head of silver hair, he is constantly mistaken for someone far older just due to his hair color, even though his facial features and skin look young. Obviously there is no right or wrong answer, just what's right for you.
I started dying my hair about 3-4 years ago. I'm actually not sure what % gray I am, but I do have a shock of gray hair at my temple (think cuella). I dye my hair every 4 weeks. I have dark hair, but at some point I'm going to totally switch to going lighter so the maintenance isn't as noticeable. I just use box coloring ... $7 and 25 minutes every 4 weeks is pretty doable to me. I'm in the category of not willing to accept looking older. I started getting grays in my teens.
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