Returning Player - Starting Fresh, need some advice
First, a little history.
I stopped playing WoW almost three years ago, with the end of Wrath, before Cataclysm was released. Arthas was dead, and I was in a casual raiding guild on an RP server that got maybe half way through Icecrown Citadel. I enjoyed the raiding experience, even when I didn't get anything. It was fun being a paladin, able to heal or tank as the guild needed (though tank was my preferred choice). After a while, the guild started to fall apart, though I don't remember why. Shortly afterwards, I ended up quitting.
I play EVE Online as well, and EVE was definitely a contributing factor to me leaving WoW. I still play EVE, and I would recommend it to anyone that loves complicated games.
At the end of last November, my boyfriend got a free WoW battlechest from something, so he installed it. I activated my old account with one of the free 10 day cataclysm trials. We played a bit, and I found that I was enjoying WoW again, even from a fresh start. I decided to take advantage of the black friday deals (online, yay) and bought a battlechest, cataclysm, and mists, and made a new account (without the really bad account name that I made... years ago) attached to my same battletag. I got to keep all my mounts, and pets, and achievements (yay), and get a fresh start.
I started playing alliance side this time, though I did roll a horde character on my old server so I could keep all my gold and other shinies from my bank alt. I now play on Earthen Ring for the RP, but I've been wanting to get back into raiding, or at least start working towards that. Unfortunately, Earthen Ring isn't a very high population server, which makes me wonder if there is much of a raiding community there... that's where tankspot comes in!
Now for the part where I want advice! (aka TL;DR section)
What would be the best way to go about getting into a raiding guild with a fresh start on a new server? Should I level to 90 wherever and start gearing up off dungeons, then bite the bullet and do a server transfer when I find a guild I like? Are there guilds that will take new characters so I can level and gear up while participating in the social part of a guild, eventually becoming raid-capable?
How does a new player, or old player starting over, get into raiding these days? It always feels like you have to be in a guild from the start of an expansion to actually take part in raiding, because everyone else has already gone past the start (even though I know it's not true, it just feels like it).