I'd known about multiboxing for about a year (I think) before I started. What tipped it off was seeing 5 alliance mages in AV when i was killing some time with my paladin. Unfortunately, the game ended RIGHT as they dismounted and I hit them with an Arcane Torrent. At the time, I was fairly confident I'd be able to take them. Now....not so much. I'm pretty sure one volley of fire blasts would have dropped me. (My pally's got solid prot gear, but I BG as ret - in greens - for kicks)

That, however, was the moment I went "Hmm. I wonder." I spent about a week experimenting, researching, and learning with friend's accounts and trial accounts to see if my computer could handle it, and just what I was getting myself into. Then I went out and got 4 more accounts, and went right from solo play to 5boxing. Now my boys (5x orc shaman <Crew>) are level 63, and I should get 64 tomorrow. I've learned a lot already, and multiboxing's made wow fun again. I was right on the verge of quitting.