I just got started reloading, I'm sure I have a lot to learn but I mayby my experience getting started can be helpful to you.
In my opinion, the first thing you should invest in before buying any loading equipment at all is the Richard Lee Modern Reloading 2nd edition. I thought this was just a book of load data, but it actually has about 10 chapters of useful reloading information. It does read a little like a comercial for Lee Products. It covers what they offer and how it works and that can be useful to choose the setup you want. Don't overlook other good books like the ones mentioned in the beginners post at the top.
I started with a lee classic loader in 45acp. Honestly it is not really practical to get a lee loader in a pistol caliber. I chose this one because my least favorite gun is a llama 1911 and I figured if I was going to mess something up with reloads, it might as well be that one, and I wanted to "test the waters" without much of an investment. The lee classic loader is slow and awkward, but it does work, and it is neat to have a pocket sized reloading kit. ( You can easily put the lee loader in a pocket, but if you want to include the necesary hammer and components, that turns into a small tool box ) A Lee classic loader makes sence for reloading rifle rounds if it is something you don't need to crank out a lot of ammo for.
My goal for reloading was to get a set up to crank out inexensive plinking ammo for my 38/357. First, when I read the "One pull of the lever cranks out one bullet" I was really excited about getting a Lee PRO 1000. I changed my mind when I read the customer reviews at Midway.com To sum things up, most people seem to think its a great deal for the money, but getting it and running requires some tricks and tweaking, the more expensive Loadmaster Pro has even worse ratings. If decide to move on too a progressive, I think it will be Dillion or rcbs. Next I decided the Lee anniverary kit was the way to go, when I called the dealer, I let them talk me into a 4 hole turret press. I am glad they did. I don't suppse there is anything wrong with the anniversary kit, but the turret press kit doesnt cost much more, works alot faster and can easily be used as a single stage press if you want to. ( you can see it in action at the LEE website ( I after using up my first hundred bullets loading up, I took off the auto index in a few seconds so now I can continue to deprime, resize and reprime until I get some more bullets )
a final note, if you go with the turret press, make sure to get the auto prime kit for it, its easy to put on and works great. I am NOT happy with the Lee Scale, it only goes up to 110, the tenths are very hard to read, and as far as I can tell, its about 4 tenths of a grain off. Next gun show I am hoping I can trade it off on a set of dies or something useful. It came with the kit so I am kinda stuck with it.