I don't mean to sound like my grandfather who had to walk 25 miles to school everyday through 10 feet of snow, but I started out 2-boxing with a rogue and a holy priest pocket healer on follow alt-tabbing when I needed heals.

Seriously though you'll have fun, its really really fun, just don't try to over-extend. Either 2-box mixed classes or 5-box all the same ranged class. Starting out with a mixed team or a melee team will be very frustrating. You need to ease into that.

I use IsBoxer and if the sub cost is not a problem I suggest just starting with that. The quick start wizard will have your first boxing team up and running in like 10 minutes.