My gear was just OK when i started boosting. I also did some arena and BGs to pick up the S2 gear. They main thing you have to worry about before your gear gets good is the size of the pulls. This you will found out through trial and error. Which for me was fun, how much can I pull and get away with it?, is a mini game all by itself. You will die, you will get over it.

One thing you need to consider is how are you linking your accounts. If the pally is on a linked account he will hit 60 with your first group, but then screw up the XP on the next set because of this link. If he is not linked then he will lag behind, 3x behind, the rest of that group. You could level him then transfer him to an unlinked account to get around this. Then don't put any more toons on his main account. Actually you could refer from that account and get him a Zevhra mount if he isn't getting on already. Then transfer him back when you are done RAFing. This is basically what I did. I use the other character slots on the account for my mules.