I prob should have explained my time and such a little better to give people a better idea. Boxing is my little side project in WoW it by far and large is not my main timesink, for that I currently have 2 raiding toons that I (try to) keep up to date in my raiding guild. I tend to only have time for boxing on weekends and even then its not the entire weekend or every weekend only a few hours each day.

Im thinking I will almost defiantly go with a dungeon team first up, they can help me build up things(Heirlooms, rep for enchants, badges for gems etc) to make the rest a lot easier. I think now I just need to decide on my tank/healer/dps combo.

So Warrior, Pally or DK tank (I just remembered I have a DK at 60 I wanted to eventually get up for tanking anyway)
Shaman or Pally Healer (Im leaning towards shaman for totems, Bloodlust and chain heal)
And Pally or Hunter DPS (Still want to keep my mages together)
Alternatively I could boost up 3 other DPS(Any class) if I really knuckled down. It would take a serious time sink but I should be able to pull it off as I have a decently geared 80 Priest to boost with.

Would be kinda funny if I went with DK, Shaman, not hunters as it would be completely different to the plan I had mapped out.

A question for when I do get my mages up, geared and into BGs, do people think it would be better to go in with 5 mages, or should I go with a shaman who can buff/heal them even if its only between fights?

Damn why does this boxing thing have to give me so many options all of which sound attractive until I think of something else that sounds awesome.