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Best way to start on a new server?
Many moons ago (well, maybe 8 months) when I decided to start really trying my hand at boxing, I decided to, as an experiment, try my hand at rolling on a new server and starting completely from scratch. On top of that, I also decided I was going to do quests only until I could get into Ragefire Chasm, and from the time I could get in, I would level up entirely through random dungeons with my team and class quests that were needed to get skills (redemption was really it). We were not RAF'd, had no heirlooms, no starting money, etc.
It wound up taking a REALLY long time, but it was a pretty good experiment, and I feel like I learned a lot about how to play, handle different types of encounters, and so on. I think I also figured out what NOT to do, if I wanted to level faster or make better money.
Unfortunately, on my server there are no other boxers - and now I'm at the point where I want to begin trying to raid, so it's either 10box (which I just don't want to spend the money on, and I think would also just end in me becoming overwhelmed) or move to another server.
I'm trying to figure out the best way to do this - I have 5 80th paladins who are mostly geared out in badge stuff, have some heirlooms for new characters (though they're the shaman mail chest and shoulders since I was so dumb I didn't realize cloth would work for everybody), and a reasonable supply of gold for now. So, if I were willing to eat the character transfer costs, $125USD, I could start with some stuff.
Alternatively I could just restart on a new server and just level ye olde fashioned way, using a group of DKs to kind of get everyone off to a quick start (gold, bags, etc).
Or I could just be a mooch and beg someone to sponsor me until I get on my feet 
So, if I did want to start over, what's a good server to be a boxer on (any active guilds, people who are willing to try raiding) and what do you guys think are some good ways to get started successfully and quickly?
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