Starting out, go single, at least for the rifle cartridges. Progressives are nice for pistol ammo, but can be a little frustrating for new reloaders.
Other advice.... get some good manuals. Don't just rely on one. If possible, find someone in your area that reloads, and see if they might spend a little tim ewith you going through a breif reloading session. Reading how to do it is nice, but actually watching is a better way of learning the ropes.
You don't need to buy all the expensive equipment to reload either. Get a medium priced or higher press and a good scale. The other smaller tools like funnels, deburring tools, and primers]ing tolls, etc., are generally the same in performance.
More advise... Many folks, including myself, recomend reloading in a clean environment that is free of distractions. many don't do it while watching TV or cranking tunes.
Double check everything at first. Better safe then sorry.
Have fun, and remember that even though it might seem like reloading will save money, you might end up creating more rounds, ultimately saving little. You can create very accurate and consistant loads though, and shooting your own ammo is a real pleasure.