After my paladin hit 70 a few weeks ago, I felt kind of ... empty. I wasn't raiding due to scheduling, I'm terrible at PVP, and I had little desire to run instance after instance getting my pally better healing gear. Then a real-life friend who lives far away suggested that I roll a character or two on his new server, Medivh. And thus, I created three new characters, one for every class I've never played (undead warrior, blood elf priest, and troll shaman.)
I'm having fun figuring out the specs and professions of my new, nearly-naked lowbies. But it's been so long since I began a serious character on a new server, I'm getting bombarded by all the issues that face new players. I don't have any bag space, or money for that matter -- I can barely afford my skills and food. Walking places seems ridiculously slow, I have no higher-level friends to run me through instances, and my new abilities are confusing and numerous.
All of this makes me wonder if for the majority of the population, rerolling (defined as starting from scratch on a server where you have no characters) is worth it. Most of us have relatively wealthy 70s, strong guild and friend connections, and an overall sense of history on a single server. If our servers are our homes, then rerolling is leaving your money and possessions behind to move to a new city where you don't even have an apartment yet.
What problems have you found when rerolling? When you reroll, do you generally abandon your character before going to Outland, or do you keep pushing on to midlevel? All in all, is rerolling worth the strife, or do you prefer to stick on one server?