One thing I haven't seen discussed here yet is cost or available space.
When I started, available space was a large consideration. I simply didn't have the space for a large, tall, progressive. Cost was also a consideration for me (a much smaller consideration), although I could have afforded any press up to about the $1000 range and probably could have stretched my budget as high as $1500. My budget was for just a press, and not all the little things needed (like dies or a scale) to actually make ammo. But the more I spent the more I would have to do without other things, hence one of the reasons to keep the cost down.
Another thing, I knew nobody that reloaded, and so I had no mentor. I had to learn everything myself from a book or the internet, and the internet can be a sketchy place to get information sometimes. And finally, I wasn't sure if I would even like it, or stick with it, and I didn't want to have a lot of money invested in equipment that could be a bit difficult to get rid of.
So it really was a no brainer for me when I found a Hornady LNL single stage kit for $200 plus shipping (on clearance from Midway). I only had to purchase dies and I had all my equipment. A pound of powder, a brick of primers, some brass and bullets, and I was on my way. My first loaded round cost me about $400, and the next 499 rounds were free (if you don't count my time).
This was about 4 1/2 years ago, and I have honestly considered buying a turret or a progressive since then, but haven't for several reasons. First, I don't shoot as often or as much as I did many years ago, so being able to load 100 rounds in twenty minutes on a progressive vs. a few hours on a single stage doesn't have much appeal because I enjoy my alone time at my bench. I also don't see the advantage (for me) in using a turret except to be able to handle each piece of brass less.
I still think about a progressive from time to time, and I certainly have the space for one now, but I just don't see a need for it in my situation. I could easily afford it, but I currently only work about 18 hours a week and really don't need the time savings it would provide. And I don't see my current work schedule or shooting habits changing any time soon.
So I really think it comes down to the individual and their current and future expected needs as to whether they should start with a ss, turret, or progressive.
My situation certainly wouldn't apply to every potential new reloader.
chris