I took one of my Death Knights and spent the weekend running instances to gear up a few of the gang. They ran Dead Mines, Wailing Caverns, Blackfathom Deep and Stocks - a couple a few times. It's actually quite fun, and only one death on the last boss in WC as I wasn't paying attention to his aggro. So all the quest greens are being replaced by blues and we're getting lots of items for the Enchanter to d/e and cloth, ore's, etc.
As I have enjoyed this on a desktop/laptop combo - in a jury-rigged fashion (two keyboards, etc.) I knew there had to be better ways to duel-box. I googled duel boxing and found Duel-Boxing.com, so I've been studying that and have been working on trying to set up three-boxing. I've downloaded KeyClone and the addon Jamba. I've started 3 lvl 1 Mages to test the setup out tonight. I think it will take some work to get things running right. I also searched YouTube - lots of good videos there as well!
I know if I'm going to I want to play different classes, not 3 of a kind. I don't have any goal of arena's, etc., it would be purely for my own entertainment!
I'm so tempted to try the 5 box, although I'm not sure my rig will take it - and I'm not sure how much I want to invest in another aspect of my addiction - lol!!! But it's tempting.
We'll see . . .