My mother used to dye her hair years ago and one day my sis and I convinced her just to leave it be. Now, at 54, she has beautiful silver and black hair. I myself, have found grey (I'll be 24 in July) and refuse to do anything to hide it. Since my mother and I have pratically the same hair type (thick,black, and curly), why prevent the inevitable; just embrace it!
I joined the short hair club 3 years ago (I cut about 20 inches off!) and have never gone back since. Long hair is great but can be a real pain sometimes. Also, I would like to think that I have the confidence to not rely on my hair too much for my beauty (but yes, I am vein enough to make sure it looks good ). Don't be intimidated by societal stereotypes of women with short hair; they are just that, stereotypes. If a man doesn't like me because my hair is too short, then too bad for him and any other person who doesn't like me b/c of what I look like!
As for dreds, if you can pull it off and pull it off right, then go for it! It is just hair and if you don't like it, you can start over again!