The Most Difficult Part of Multiboxing is...

[Klamor]

you could 4 box and go with

rip
slip
brush
ahh

[Sanctume]

(Shaman + Pally + Warlock)
Azzhat + Aszhat + Azshat
Come + Honor + Face
Eye + Luv + Ewe
Ohh + Mah + Gad
Ell + Ohh + Elle

[Stabface]

Dallass
Corbinn
Leluuu
Multii
Paass

<Big Badda Boom>

[Tehtsuo]

(yes, it's against the naming policy to use ñ ù â etc, on US realms at least.)

fyi - No it is not against the naming policy as of 2008. Check the Blizzard site, there's no mention of it. I also asked on the customer service forum and confirmed it is no longer against the naming policy, hence the names of my team.

[Chorizotarian]

I considered all kinds of mildly funny crap. My best one was:
Everybo
Dywas
Kung
Fufigh
Ting

I figured that when I got comments like, "omg u bot u so reproted (sic)," I could just hit my spread out macro and /dance with them. In the end I went with logical names though:

Pally: Iaggo
Shammi: Katator, Ketator, Kitator, Kutator

I like to pick names with a different starting letter for all my chars so that mail auto-complete pulls them off my friends list with 1 key. For the shammies it will take 2 keys, but I like that the names are logically organized.

I also followed Xzin's suggestions about creation time:
Kutator < Kitator < Ketator < Katator < Iaggo

That way my pally main appears first in the group and the 4 shammi are alphabetical. If I spec one resto I'll do Kutator so that the main healer is the last char in the group.

[Atorifan]

PVP oriented

ican

haz

honor

nao

[Klamor]

though this might be funny for just multi :

shenan - igans

[Eteocles]

I had no prior knowledge of this thread when I named the hunters in my sig. >.> I usually stick to the main and beginner haven forums lol; I like some of the 5set names above, Come Honor Face was pretty funny if bad

It's true though...I have enough trouble naming one char let alone 3, and it wouldn't sit right with me if they didn't match in some way and I'll never use the "a b c d" crap It'll either be re-spells or themed names for me

[Marathon]

Ok I had couple of Tauren Shammys for awhile names where as followed:

Acrunk & Bcrunk

Guild name was "Meet tha Crunks"

I assumed that when I was able to I would add 2 more shammys - Dcrunk and Ecrunk
With a female pally tank called Countescrunk.

But it just hasent happened yet.

[boxer]

Seinfeld reference:

Jerry
George
Kramer
Elaine
Newman

Power Rangers:

Jason
Zach
Trini
Kimberly
Billy
(or a warlock named Megazord lol)