Can you connect 2 iPods at the SAME TIME to iTunes?

I have a HUGE music library and I have 2 60 Gb iPods. I manage them manually. I'd like to connect them BOTH, AT THE SAME TIME , to make it easier to make sure they have totally different songs on each of them, and remembering is out of the question :-}. I would have to connect them both simultaneously, and be able to drag songs to either of them. Can this be done without problems?

Welcome to Apple Discussions.
From what I have heard, it is possible to do so. I have never tried to do that, though, so I have no experience on this.

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