Go with a progressive press. You can still learn to load from using a progressive. I started on a progressive (specifically a Dillon 650), and I once used a single stage for competition shooting. You should start on a single stage if your goal is to turn reloading into a time consuming chore that makes you hate reloading.
It is a fallacy that using a progressive doesn't teach you about reloading. With a progressive, you still have to do and learn everything that you would do and learn in a single stage, but the difference is that you will do it quickly and efficiently.
If you learn to use a progressive, you will love reloading and have fun with it, like I do.
Any of the progressives are good. I would pick one that has auto indexing and uses standard dies. Again, I believe in making reloading as easy and efficiently, as possible, and auto indexing really helps with that goal. The Dillon 550 doesn't have auto indexing.
There is nothing wrong with starting off with a high end machine. Go with the Dillon 1050, if you can afford it. I load on four separate 1050s, and I should warn you that it takes about 60-90 minutes to change and adjust calibers (which is why I reload on four different 1050s...caliber change on them sucks). Complexity, and the ability to adapt and learn from that complexity, will force you to become better at what you do.
After you pick the progressive, then it is time to pick a bullet feeder.
Single stages are good if you intend to only shoot four cartidges a year, anything above four per year, go with a progressive. Ok, I exaggerate bit; make that seven per year...