Learning Curve

[traedoril]

Question: How long does it take to get to where playing multiple characters is second nature? Sometimes I'm thinking "this would be easier if I were just playing the one" but I need to take advantage of the RAF bonus. I'm guessing I just need more practice or some tips on actual gameplay - I've already implemented all the technical stuff like keybinds and addons and all.

Getting acclimated to multiboxing is actually on a person to person basis. I started by dual boxing a blood DK and Disc priest from level 60 - 85. Once I learned how to heal it took me 2-3 hours to get used to it. When I turned to 5 boxing it was like relearning the game again. It still took me only about a week of research and practice to get comfortable with it.

Question: I know this is one of those "play what you like' questions but is there a standard class/spec that is sort of like the training wheels for dual-boxing?

I am weird in this aspect. I acutally play 5 different classes and with a little research found this not to be much more difficult than playing with all of the same class.
The cast sequence macro's and the 2-step keys don't change for boxing different toons and you dont get kicked from LFR/LFG because I have a different name for every toon and I do good DMG/Healing/tanking on them.

Everything you do is gonna take practice. You can be better than 5 individual players or you could be the worst boxer in history. Keep working with macro's and key maps and you will perfect your playing style.