In my opinion, the best place to start would be 2 casters of the same class. when you get into multiple classes (especially a melee and caster combo) you will have tons of problems setting up the keys and macros.

Just create a trial account and start a couple of mages using your current account for one of them since trial accounts can't create groups (but can be invited to a group by a non-trial account). It will be the easiest to setup since they will be the same and there are no melee actions to get confusing.

Octopus setup - http://www.dual-boxing.com/wiki/inde...topus_Tutorial
or this one... http://octo.sourceforge.net/