Ok I'm one of the Dillon fans. It's what I started on, took my time and went slow. I guess it all comes down to how much you will be reloading. If you are reloading 100rds a month than a single stage would suit you just fine. Any more than that a progressive will save you a lot of time. Dillon has the best warranty in the business.
Try both see what you like.
I agree with Xd357. It does come down to how much ammunition you want to reload. I started on a Dillon and know many other folks that did as well, and I have yet to have a need for a single stage. Not everyone wants or needs high volume and that is fine, but if you do want or need high volume, why start off with something to learn on just to get rid of it or put it to the side in a short time for something you could have started with in the first place? If you want to load up a couple hundred rounds of each caliber each year, a single stage will do it and cost less money but more time. If you want a couple hundred rounds per month of each caliber, cry once, spend the money, and you will be happier each and every time you load.
If you can find someone close, I like the idea of trying both first. If a progressive overwhelms you, then by all means don't start out with one. It's not like they are rocket science though. I think the most important things, whichever press you start with, are to get help if you can, ask questions, and make sure that you take your time and pay attention to what you are doing. If you can't sit down without distractions or without giving it your full attention, wait until you can. My $.02.
PS: There is a USPSA match in Byram this coming Sunday morning, 6/6. Directions and some info is available at http://www.teammagnolia.com
. Whether or not you are interested in ever competing, if you'd like to come out there will be a lot of high volume handgun reloaders present. I imagine several in your area would be willing to help or let you come by some time and check out their progressive presses. Just something to consider. I plan on being there. Feel free to send me a PM if you have any questions or think you might make it.