i got into reloading this year, and picked up a RCBS rock chucker kit for $300. they have a $75 rebate good until the end of this year if you buy $300 or more of their stuff(i still need to send mine in

), so that takes the sting out a bit. you can certainly find good deals on used stuff, but the kicker is that when you're starting out you probably don't know exactly what you want so it might be easier to just buy a kit.
in addition to the kit, you'll want to buy a powder trickler, and if you want to use the nice powder measure that's provided, i would recommend buying a stand for it(just seems like a real hassle installing it on top the press). the powder measure would be nice for loading pistol rounds, but i don't use mine much since i mainly reload for .264 magnum and the powder i've been using doesn't meter well(i use a lee dipper set to throw charges and then trickle them up to what i want).
all and all, i like the kit, but if i did it again i'd consider a turret press with extra turrets, so i can leave my dies adjusted to save time. in the future i'd really like to invest in a chronograph and some headspace/OAL gauges as well.