LoL, Fur...

Assuming the original poster has actually played WoW before (unlike someone who shall remain nameless), and given that the OP has "huge swathes of freetime", this wouldn't be very hard to do. It has been my experience that with a group of five characters it takes about 8-11 (/played) days to go from 1-80. If you have R-A-F and can skip the first 60 levels with some toons, then you'll knock off about 16-24 hours from the timer. For simplicity, lets just say that it takes you 10 /played days to go from 1-80. In other words, every 240 hours, you have a new group of 5 level 80 characters. We don't know how much freetime you have, but lets assume you're playing for 80 hours a week. With this timer, it would take you 3 weeks to hit 80 on the first team (5 characters every 3 weeks). We have about 36 weeks left before the year end, 2009. 12 sets of 5 characters (60 total characters) would put him at around 36 weeks. Since the above figures don't include characters that have been granted levels (this can really change the total amount you'll need to play if you can start 25%+ of your team up at level 60), I could see this being possible.

The only downside is that you'll probably get burnt out about halfway through this, and you won't have any decent gear.