I have terrible handwriting also. However, I prefer to handwrite my letters as I think you are giving something personal to the person you are requesting autographs from. I have experimented with typed letters, and not seen any difference in the level of replies, so at the end of the day it is what you feel most comfortable with. Either way, you should get replies.
Content is fairly simple. Start with a simple opening. I always begin with -
"I hope this letter finds you well."
After this, I then talk about what I like about them or their work or anything else that caught my interest and prompted me to write.
I then ask for the items I have enclosed to be autographed, and mention I have included a postage paid reply envelope. Sometimes I use this as an opportunity to talk about the item(s) I want autographed as well.
Then I sign off.
My sending patterns depend purely on how much time I have to write letters, and put the requests together. This normally means 4 to 5 requests each week, sometimes more, sometimes less. I never plan to send a set number of requests. The letter writing is part of the fun for me, so I like to do this in a relaxed manner, and not force it through to meet a self set deadline or limit.
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