Zach,
I started with the anniversary kit about 8 years ago, and liked it alot. I just moved up to a Dillon 550, but keep the Lee press mounted to my bench because i use it for 30-06, 300 winmag and 270. If I only want to load a box or 2, the Lee press is the one I use.
Most of the time, at least one of the online stores will have the anniversary kit on sale for $69.
If you're not a benchrest shooter, like most of these fellows are, the Lee will do everything you ask it to...and very cheaply.
If you need dies, keep an eye on E-bay. I've seen SEVERAL really good deals on RCBS and Hornady sets (under $20) over the past few weeks. I would have bought them....if I didn't already have those calibers.