Pick up a couple of reloading manuals. Along with reloading data, there is usuallya section for the "how-to's" of reloading. The most recent Sierra manual is my go to as of right now. The latest Speer is also a good manual.
How much you plan on loading is going to determine the type of press. You can do quite a lot on a single stage press, but it will take a large chunk of time. The progressives are miles ahead in speed and can put together the same quality of ammo if done right. I loaded around 15,000 rounds of .45 ACP on my RCBS Rockchucker before moving to a Dillon RL550B and I'll never go back to the single stage for high volume handgun cartridges. I still like to use the Rockchucker for rifle rounds and some handgun rounds, so I won't be getting rid of the single stage anytime soon.
You might try and find someone in your area that reloads and have them show you. Hands on is the best way to learn, plus you'll have someone with experience watching and showing you all the little tricks.