So I just hit 54 last night. I have found that my first attempt at 5 boxing I swung for the fence by selecting the following classes:

Paladin - tank
Druid - Healer
Shaman- DPS
Warlock - DPS
Hunter - DPS

I have found that my PVE experience and ability is unmatched I have not however; spent much time in the PVP realm. I do not believe I would fair to well in arena or battlegrounds with this makeup. I have a friend who has a team of 5 shamans at 70 we are anxious to make attempts at karazhan. I obviously have a lot of work to do before I get there.

Anyways curious if any of you have chosen the road less traveled by selecting 5 separate classes and if so what macros or tips/tricks you use to accomodate your group make up.