Some people purchase high quality photos to be autographed.
Another option would be printing your own picture (I suggest thick paper) these usually turn out very well.
When you send it out most people write/type letters asking for an autograph.
If you want it personalized a good thing to do would be explain your friend's situation. In your letter ask if she could put his name on it.
Not every celebrity does this but many do


Hopefully this helps some
Good luck!

Hi

http://www.fanmail.biz/9120.html

Fanmail

Hello Everyone,
This is my first attempt at getting an autographed photo, so please excuse my ignorance. I have a 57 year old friend that has a HUGE crush on Marie Osmond. He was diagnosed with MS a couple of years ago and I wanted to get him something special. He goes crazy every time he sees a Nutra System commercial. So much so, that he texts me every time one comes on as he's watching TV during the day. HOW DO I DO THIS? I have no photo to send in to the fan club. I would like to get it signed personally to him. Can anyone help me ease this mans love sickness? Lol. Thanks in advance.