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I'm not really new to the autograph scene, but I've never done a VV before, how do I know when to send it out? If the venue is only 3 hours away from my city, when should I send it? The performance is August 17th, so should I send it on the 12th or what? I'm not sure on how to judge this.

I would send a week or two out to make sure that it gets there on time. Seeing as how the 12th is tomorrow, I'd probably overnight it or send it 2 day mail to ensure that it gets there on time. You have to figure with venues that they receive it in their mail room, process it and then pass it to the appropriate people. God only knows how quickly their mail people can process things. Hopefully it doesn't sit in the mail room for more than 1 day. Good luck to you!