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Do you have (or plan on getting) other guns in other calibers? Do you plan on shooting more than a few times a year? If so, you will save money in the long run and have better and/or customized ammo by reloading. You may not save money the first batch because of tool costs, etc, but saving over time is another question. I'm sure I have spent into the thousands on reloading tools and gear over 30+ years, but I'm also sure I've still saved money in the long run. And I can make much better ammo than I can buy, especially when you start talking rifles and long range shooting.
I always hesitate to encourage a beginner to get a progressive press. There are just too many things that can go wrong and using a progressive just amplifies the risks - too many things to watch for at the same time, including things you may not even know to watch for yet. I strongly suspect that most KABOOMS caused by bad ammo involve a progressive press - not because there is something wrong with the press itself but because it requires more skill, more knowledge, and more concentration to use. It's like almost any kind of work - you don't start out with the most complicated and expensive tools, you work your way up.
A good single stage is great to learn with and will last a lifetime. If you move into rifle loading, you'll want the single stage for that anyway. RBCS makes a Piggyback unit that turns a single stage Rock Chucker into a progressive for pistol loading. It's not as sexy as a Dillon, but it works just fine and costs a lot less. I own at least 5 presses and I still use the first one I ever bought.
My suggestion is to get a Lyman Reloading Manual and read it carefully. It will explain every step of the process, what each tool does, and why you need or don't need each tool for a particular type of cartridge. After you understand what's going on, then you can answer most of your own questions about which tools you need to get started. (There are several other reloading manuals, but IMO the Lyman book gives the best explanations.) Lots of guys have lots of opinions on which brand of tools is best, but really almost any of the major tool brands can serve you well. Lee makes a good Classic press, but I can't really recommend their other tools. There's a reason they are cheaper than anyone else (just my opinion based on trying them and almost every other brand out there).
ETA: I agree with the other guys about joining a forum that concentrates on reloading. I recommend Handloads.com mainly because there are lots of experienced members in all kinds of ammo AND I guarantee you won't get any flaming or arguing that you tend to find most other places.
I always hesitate to encourage a beginner to get a progressive press. There are just too many things that can go wrong and using a progressive just amplifies the risks - too many things to watch for at the same time, including things you may not even know to watch for yet. I strongly suspect that most KABOOMS caused by bad ammo involve a progressive press - not because there is something wrong with the press itself but because it requires more skill, more knowledge, and more concentration to use. It's like almost any kind of work - you don't start out with the most complicated and expensive tools, you work your way up.
A good single stage is great to learn with and will last a lifetime. If you move into rifle loading, you'll want the single stage for that anyway. RBCS makes a Piggyback unit that turns a single stage Rock Chucker into a progressive for pistol loading. It's not as sexy as a Dillon, but it works just fine and costs a lot less. I own at least 5 presses and I still use the first one I ever bought.
My suggestion is to get a Lyman Reloading Manual and read it carefully. It will explain every step of the process, what each tool does, and why you need or don't need each tool for a particular type of cartridge. After you understand what's going on, then you can answer most of your own questions about which tools you need to get started. (There are several other reloading manuals, but IMO the Lyman book gives the best explanations.) Lots of guys have lots of opinions on which brand of tools is best, but really almost any of the major tool brands can serve you well. Lee makes a good Classic press, but I can't really recommend their other tools. There's a reason they are cheaper than anyone else (just my opinion based on trying them and almost every other brand out there).
ETA: I agree with the other guys about joining a forum that concentrates on reloading. I recommend Handloads.com mainly because there are lots of experienced members in all kinds of ammo AND I guarantee you won't get any flaming or arguing that you tend to find most other places.