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If your prices are about the same as mine, a loaded round costs between six and seven cents per round, not including the cost of brass. That's about the least you can spend on a round of .38 special unless you cast your own bullets from very inexpensive lead. If you don't use a crimp on the bullets and aren't prone to losing brass, 38 special brass will last a very long time. Figure around $20 for a box of 500 bullets, $16 for a thousand primers, and $17 for a pound of powder.

If you're shooting a lot, get a progressive press. You can't go wrong with Dillon. My critical point was when I was shooting more than 100 rounds per week. After that I wanted something faster because I didn't want to spend a lot of time reloading. It'll be more than $350, though. You'll want to get extra primer tubes and a maintenance kit and spare parts kit for the Dillon. Figure around $50 for that. You need a good scale and a caliper, figure another $100 for that. It's worth it to use Dillon dies in a Dillon press. They really are easier to load with. You'll also need shop glasses. Realistically, you're looking at about $600 to get set up right.

If you've got an indoor range nearby you may want to ask them if they will sell you used brass. I get mine that way and it saves a lot of money.

You could also do like a lot of guys and get set up wrong the first time, in which case you will pay to get set up wrong and then pay again to get set up right.
 

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Mikey brings up an excellent point. Cabelas sells bulk 38 special ammo at very good prices. If you think Cowboy Action may be a passing fad with you, you may want to buy a couple of thousand rounds of the low cost 38s and use them for a year. If you decide that Cowboy isn't something you want to stay with, then you've saved the considerable expense of buying reloading equipment. If you decide you like it, then you've got a good supply of brass to reload.
 
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