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Sending CD insert 2 a performer ttm via venue, is that a good idea or a bad one? I was thinking about doing it for Rihanna.

I don't see a problem with it but just remember you might not get it back. If you're okay with that, go ahead and send it.

I do not understand why they would want to keep it, doesn't serve them anything

There would be no problem sending it, as long as you are sure you want to even if you might not get it back. Actually, the recipient might not always keep it. In some cases, the venue may not forward mail(rarely, however).