My opinion (like armpits, I have 2 and they both stink (to others)) is that every fledgling reloader needs a mentor. 33 years ago, I sat, newly married, constantly underfunded, on the floor of our apartment with a Lee Whack-A-Mole tool, reading the instructions as I beat the daylights out of 2 boxes of 357 mag cases and by trial and error assembled some of the most consistently poor ammo ever to be fired in utter joy. Realizing I had a poor teacher, I attended a reloading seminar hosted at a local store by the RCBS rep, learned a few of the errors of my ways and bought the RockChucker, Ammo-Crafter kit, dies for a couple of pistol and rifle calibers, etc. and launched. I still have all that gear, I still use it all. I still made mistakes, but I never stopped learning and improving, and I never made a particularly dangerous mistake, like an overcharge, or a squib. I owe that to the hands-on detail oriented methods of reloading essentially one round at a time.
Times and spouses changed, as did disposable income. USPSA/IPSC shooting entered my passions list and the necessary quantities of ammo increased exponentially. The rage at the time was the Dillon RL-450, that numeric designation hinting at the rounds-per-hour capabilities of the machine in the dextrous hands of an experienced reloader. I checked: 500 was possible, 400 was a more reasonable rate. I produced lots and lots of pretty .45 ACP ammo... as well as flipped primers, crushed brass, spilled powder, and the dreaded squibs. All entirely my fault. I'm a DIY kind of guy, so I figured it all out on my own, and of course, with the helpful hints of cohorts, gun shop groupies, manufacturers' techs and the like. I checked my need for speed at the door somewhere along the line and settled into a routine of checks and balances that allowed me to produce consistent, safe, quality ammo, and by slowing down actually got faster and more efficient.
When I got interested in casting my own bullets, I cut to the chase and found a mentor. I spent several sessions casting with his gear, learned about proper techniques and equipment choices and got a faster start down that path to success. That learning curve looks so much better.
To tie this diatribe back together, as far as equipment choices go for a newbie, I vascillate in my opinions depending on the individual's mechanical abilities, work ethic, and study habits. I personally advocate learning reloading from the basics, perhaps a single-stage press or a turret to get that real, in-your-face, hands-on experience with all the steps and components involved. That experience is invaluable when it comes to troubleshooting any form of reloading. I've never upgraded my progressive reloader beyond automatic powder and priming, because I still feel that by setting cases and bullets manually and using my fingers to index each round, I somehow have better quality control than those slot machines that poop out one round after another every time you pull the handle. And with fewer mechanical linkages, I think there's easier recovery from a somewhat catastrophic failure. That said, about ten years ago, I mentored my best friend in the ways of reloading, starting him with the slow and mundane, working up to the progressive. His first personal tool was a Dillon RL-650 with every freaking bell and whistle they offered for it and he has seldom had any real issues. I believe that's because he had a good learning foundation that familiarized him with the intricacies of reloading. You can't trade on experience. He has since mentored me in the use of that press. I guess it's okay.
Reloading is a lifelong endeavor, the equipment you buy will outlast you, and regardless of what you start with, will forever be useful. Several gun shops offer reloading classes or clinics, or can refer you to an experienced local who will take you under their wing. The knowledge you gain from try-before-you-buy will make your personal equipment decisions more relevant and rewarding.
My 5 cents (adjusted for inflation).
mike