Why? It's still one button isn't it? Sounds like a legitimate challenge as well as a genuine bit of fun. Are there any reasonably early points in the story that strike you as a roadblock for this? I've never been one for alts so I can't really remember the storyline trials beyond the 4/8man ones which kind of fall foul of the no carry thing.
Name me some content and I'll see what old gear I've got to have a crack at it <3