Get the Rockchucker kit plus dies for all your cartridges. You will find it irritatingly limiting for the high-quantity chamberings, but just wonderful for the 30-06. If you do a lot of the 30-06, you will never regret having the RockChucker.
An alternative choice for a $300 kit is the one built around the Lee Classic Turret by Kempf's gun shop for $220. You will have to add a manual, scale and calipers, but it comes with one set of dies included, so right around $300 will get you started. The Lee Classic Turret is fully capable of 30-06 and will triple the quantity throughput of the single-stage RockChucker if used with the auto-indexing turned on. Sue Kempf is an excellent advisor.
While you learn to load, you will also learn your loading style and collect enough information about gear to make the next choice more fully informed by experience of your own on top of the experiences of others.
Have a look at this thread. You share some of the same questions.
http://thefiringline.com/forums/showthread.php?t=515846
Lost Sheep