It depends on what your goals are and how much you're willing to spend.
You can start with a Lee Handpress kit ($25.99 from
www.midwayusa.com), add dies ($20.69 for each carbide 3-die set, $27.99 for the 4-die set with separate crimp die) and that's really all you need. You'll use the dipper that comes with the die sets to measure powder (and you
won't get a max charge.)
The RCBS Rock Chucker Supreme Master Single Stage Kit goes for $245.99, less dies but will do more (especially in the matter of resizing tough cases) and includes a scale and adjustable powder measure.
The Lyman T-Mag 2 Turret Press Expert Kit at $314.99 (less dies) is a step up with a self-indexing 6-hole turret -- you can set up two complete die sets on this one and leave them set.
From there, you could go to a progressive reloader -- for about twice what the Lyman would cost.
The first two choices require you to change out dies for each step of the process -- you screw in and adjust the sizing/decapping dies and size your cases, then install the expander die to flare the case mouths (and you re-prime the cases at the same time). Then you unscrew that die, install the bullet seating die, and finally go to the crimp die.
With the turret press, you can install all dies at once -- even for two different cartridges -- and your reloading is speeded up quite a bit.
The progressives automatically index the case holder with each pull of the handle. At the first pull, the first case is sized and deprimed, then the case holder moves. You insert a second case, pull the handle and size and deprime that case -- while the first case is primed and flared at the same time. Or in other words, you keep feeding in cases, and a loade cartridge pops out at each pull of the handle.