Two things have helped me with restringing guitars.
The most important was my purchasing an Ernie Ball battery powered string winder:
http://www.stringsandbeyond.com/erbapobapost.html When I first saw these for sale, I wondered why anyone would need one. Then I watched one in use and realized how much more control a person has with this powered string winder. The control helps keep a person from nicking up the headstock.
The 2nd thing that helps me is wearing some very lightly powered (1.25X magnification) reading glasses. They help me see what I'm doing better and protect my eyes, just in case.
The string winder is by far the biggest help.
Regards, Glenn