If you bought one box of everything you liked when you first started, then you'd have alot of WTS threads in a couple years.
This is an odd time. Usually I would say wait a while and buy a box of special smokes. Go high end and listen to other inmates advice. That way you're less likely outgrow your first box.
With all the talk of tax hikes though, I would have to say if you can afford it now buy a couple boxes of great smokes. Stay away from the cheaper stuff...5 Vegas, Perdomo, etc. in a year you'll wish you saved your money for something else.
I'd recomend a box of Anjeos, Ashton VSG's, Fuente Don Carlos, Pardon 64's, higher end Tat's
Odds are that soon you'll be getting into these anyway. It's like people say around here, once you start down the slope don't bother with Humidors, go ahead and buy a cooler. It'll save you time and money.