I started with an RCBS Rock Chucker Master Reloading Kit about 10 years ago, and haven't been sorry. I load over a dozen different chamberings, but 30-06 is one I load the most.
If you go with the Dillon progressives, you're in for a LOT of extra hassle getting set up. Don't get me wrong: if you're thinking of high-volume reloading, it's worth the trouble, but I'd still only go that route only after I'd done time with a single-stage press mastering the basics. Bottom line: you won't lose your investment if you start with a good single stage press kit and then figure that the progressive may or may not be down the road for you later on.
Every press has its fans and its detractors. Some like green paint, some like red, some like blue. I just picked green, because at the time RCBS kits were very cheap at Natchez Shooting Supply-- they may still be. If you are able to get some perspective on reloading, you'll see that each reloader's methods are somewhat different, and each press is tailored to fit only a certain range of methods. If you luck out like I did and are able to adapt to your first choice, you think your paint job is the greatest in the world. Some aren't so lucky and have to go looking for a different color of paint. Bottom line: if you've tried two different colors of paint and are still suffering extensive reloading pain, it's you that's deficient and not the presses.
If you start with a single-stage, it will help you master the basics. Later, if you go with a turret or progressive, you'll find you're still going back to the single-stage for small batches, and off-line procedures like de-crimping military brass. Progressives are a bear to set up, and a bear to change over to another cartridge. They only make sense if you are planning on turning out large batches. Loading up 20 rounds to take to the range ends up being a major exercise.
As far as dies are concerned, I can tell you that the standard RCBS dies have been great, but I would stay away from their X-Dies. There is a short story and a long story associated with my history with X-Dies. The short one is that the shaft of the sizing die was forever snapping on me. RCBS was great at replacing it, but after 4 breaks over a few years, I threw up my hands and bought a used RCBS standard resizer off EBAY. The long story? It's long.
The bulk of my dies are RCBS. I have a couple of Dillon and Redding and Lee. They're all just fine. Lee dies are cheap, but workable. I've bought a few in order to try out some cartridges that I would not have tried otherwise. I especially like their crimping dies. If you find a need to crimp, don't use the RCBS 2-die set to do it. Buy the Lee crimp die and do it as a separate process.
The other piece of info I can give you is that the standard method of capping included with the Rock Chucker was not to my liking. I don't like tubes of primers. I bought a RCBS hand primer and never had a problem after that. A lot of folks swear by the LEE hand primer too. Come to think of it, the RCBS RC Master Kit now comes with the hand primer-- never mind.
Beyond what came in the Master Kit, I bought a nice set of calipers, a set of checkweights, a vibratory cleaner and a case neck lubricator kit-- most of it was Frankford Arsenal stuff from Midway. Over the years, I've continued to use Natchez Shooting Supply, Midway, and Grafs for the majority of my reloading purchases. Most of my brass comes used off Ebay.