Hi and Welcome,

Though there are many who two box and some that 3 box, I'd say if you're already looking a 5 or 10 boxing you should just go ahead and jump right in. RAF is the way to go. Just make sure that you use the code they send you to start the trial account . I five boxed right from the start. Be prepared for those who are ignorant to make comments .... good and bad.

I'd re-spec / dual spec your druid feral then boost your new toons to 60 via instances. You should be able to do that in a weekend of committed game play... just make sure you have the gold to buy mounts and spells at 60. About 300g per toon for your first two mounts and spells 1-60. Shammies are a great way to get your feet wet. They offer decent burst dps, fear protection via tremor totems, knock backs, AOE with fire totems, healing, reincarnation, and rez's.

There are a few good software programs out there that range in price from free, to a subscription based payment. At this stage not knowing how things work makes making that decision a bit difficult. If you ask which one is better, be prepared for a few different answers. Everyones taste, and ability, is different. There will be plenty of people willing to offer you help. I've used Keyclone, and ISBoxer. Both are very good, but I'm using ISBoxer and Innerspace right now. I find it fits my needs quite well.

Like Khatovar said, this site is full of good information. The wiki is a great place to start.