I only ever send one thing to be signed except when I wrote to Lesley Garrett. I included 2 IC's because my friend wanted her autograph too but I told her that in the letter.
There are some celebrities I have written to and then gone on to meet IP so I do have multiple autographs of some celebs

The maximum amount of photos I have sent is 3, plus a questionnaire. Usually I just send one though. I have once gotten eight autographs from The Saturdays, as I wrote a long long long LOR to them. They supplied some of the photos.

Typically I only send one photo with my requests. I have sent to several celebrities more than once. Usually it's because I send VV, after I had already written via their agency. I only send VV if there has been positive feedback. Sometimes I resend if I didn't like the photo I sent with a previous request, or if I hadn't heard back from another request in a while.

Khackdrums

90% of my requests are singles. Two maximum. Mainly because I think you will get a higher response rate; but also because I am particular about which one I want signed (if I send 2) and if they only sign one they may choose to sign the one that was my second choice.

I uually only request one autograph, but have sometimes (to atheletes) sent 2 sports cards.

This is just me being curious as I have never sent more than one LOR/picture per celebrity (the only celebs I have more than one autograph for are the ones I met IP).

What is the largest number of autographs you've requested from one person? Why?