I think it would be pretty. You shouldn't worry regarding your skin tone, I think only really light colors, like blonde, look odd on people with tanned skin. However, a reddish-brown color is really pretty and would go well with any skin tone, in my honest opinion. You should definitely go for it :)
I think little lioness, your hair color right now is AWESOME but since the thought has managed to creep into your little head there I'm sure it's not going to leave unless executed lol so go ahead and do it, you'll make the color you dye your hair proud :-D and yes the color will suit you well :-)
I'm a guy so take this with a grain of salt, but I'm going to say no. I think you're right about most people with that hair color having lighter skin. I can't really tell how tan you are from your profile but I don't think mahogany would complement your skin. If you do dye your hair, how long would it take before you can dye it again?
My feeling (and photographic imagination) says that would look nice on you. It's just a coincidence but this afternoon I was taking a walk and a Spanish speaking girl on a bike passed me. Her hair was the colour you intend and her skin colour was like yours or even slightly darker. And I can tell you she looked nice :-)
I would think you look good with anyone of the colors you don't want too much burgundy to come through i think it would look good with your skin color which is olive your very pretty by the way so you should have no problem