I tried dual boxing after seeing Keyclones 5 mage video. Running 2 shammies and having a blast, but then when I wanted to expand, I didn't want to pay for expansions, so I brought in 2 mages. I found that with the exception of having to track 2 more followers and make sure they face the right direction, it was no harder to run than 2. So with regards to your question, as people have already said, if you get to feel you have mastered dual boxing 2 toons, 5 would be cake.
Beware the addiction though. Oh, and beware the times you'll log in only your main raid toon or something to run dailies, and try to hit your MBing "heal" key when he gets in trouble. Not that I did it, I mean I heard it, er, read it here....yeah that's it, I read that someone did that.
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