I recently purchased a Dillion 550B and have yet to use it, seems too complicated, I even got all the extra tool heads and dies for 9mm, 357, 45, 44, 223 video etc. But it has a lot of moving parts. I would start with a kit but load one stage at a time at first. Anyone know of a gunshop that had presses set-up to demo the process. To me hands on is better than the video.
This is exactly why I bought the Dillon video. I consider the video to be a critical piece of the equipment because it literally goes through every single step of setting up the press.
Learning to setup dies for the first time is complicated enough on a single stage. Add in the setup of a progressive and you are really taking on a project, especially when you have to switch from something with small primers to large primers.
As far as the progressive vs progressive goes. I hear good things about the hornady's, but I don't like that they auto-index (automatically moves the case to the next position whether you like it or not). I can see why some people would like it, but there are times when I work my 550B just like a single stage and I don't want the press moving things around for me. For the flick of a finger, I'd just the same do it myself, but that's getting pretty nit picky. Either one would serve you just fine.
As far as a real life demo goes, 21st century firearms (site advertiser) is the only gun store I've been to that has Dillon 550B's setup at the store for people to look at and learn how to use. I think that says a lot for them and their staff is very willing to help.