My husband's good friend, who is also my friend (I knew him before I knew my husband actually, he's one of the reasons we met) is also a huge fan of this actor. Said actor was the voice of his favorite character in his favorite show.
I'm not guaranteed two autographs.
-Be selfish! Even if you get both autographs, make them both for yourself! You're the one going all the way there and waiting in line for hours. Plus, you love half his characters and can't pick a favorite thing for him to sign anyway.
-Be the good friend and great person! Get your stuff signed first, but wait in the second line to get something signed for your friend, then surprise him with it when he least expects it.
One more question: going to a celebrity signing, is it in poor taste to print up a picture on your computer/photo printer for them to sign? Since this guy voices anime characters, I don't have any way to get an 8x10 glossy except to print it myself. And if I wanted to get something for my friend, I would need to print it myself. It wouldn't be the actor's picture though, it would be his character.
Sorry for the tl;dr.