As far as where I'm going and what I'm doing next now that Ironstevo has hit the end of the beginning, I've thought this out pretty thoroughly. I'm still afraid to head to Outland, the mobs there hit a bit too hard for my liking and I don't want to take any unnecessary risks. Since last night I've finished most of the quests in Blasted lands and have moved over to Silithus where Ironstevo actually just hit 61. The mobs only give 10% of the xp they otherwise would before level 60, however the quests still give full xp so I plan on exhausting every old world quest I can before heading to Hellfire Peninsula. If I can get to at least 62 before I head over there I think I'll stand a much better chance.
The new Ironsteve kittie version 1.0 is doing a little better since I posted last. He's almost level 30 and has a renewed bit of hope that this challenge might actually be possible now that he has his beloved Faerie Fire. Whenever Ironsteve finds a rare he starts the pull off with a few ranged abilities: Starfire, followed by a Moonfire and Insect Swarm. From there he pops a Rejuvenation and Thorns on himself and pops into bear form where he then starts using Faerie Fire whenever its up while keeping up Demoralizing Roar. Ironsteve only has a few abilities in bear form right now, and if not for Faerie Fire he probably wouldn't stand a chance against pretty much anything. In bear form it does 3-4 times the amount of damage as Maul. So long as I stick strictly to hunting rares around his level and green quests with him, I think he could definitely stand a chance.