What Shev and Gergel said.
The combination of the game mechanics in this expansion plus the unique real life schedules just makes it impossible to level up together unless you live in the same house and are willing to adopt the same steps and decisions within the game.
Also, roleplaying all the way to level 100 seems like an herculean task in my opinion.
All in all, I believe that Draenor will be a very hard place to have RP events in, since a lot of places are phased accordingly with if you've done the quests in that area or not.