Brian -
Welcome to THR and reloading.
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First... read, read, read. Even checking your local library can save you some money. I bet your boss has some books he'll loan you too.
• Realize that your shooting volumes must support buying bullets and primers in volume. By that I mean 100+. As was said above, if you shoot 20 a year it's probably not worth it.
• OTOH, if you shoot a local pistol competition, then running through 200+ per week is no problem. Even if you had to buy another pistol, say a used 9mm, all your other calibers can "piggyback" off the press paid for by the 9mm.
• Reloaders also enjoy much greater accuracy, so maybe the cost is justified by that added element alone.
• Most reloaders are happy to let you see the process and let you use their equipment under their watchful eye, just to make sure "you get off on the right foot".
• Using your boss for the "mentor" function above could be career enhancing or career limiting.
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The second thing, with all the above being understood, then is to have a goal in mind. "I want to join the bulls eye competition on Wednesday nights." "I want to join the IPSC competitions on Saturdays." "I want to join the monthly long distance rifle competitions." This because reloading is most usually a means to a goal, not an end in itself. No one simply wants to reload simply to fill their basement with loaded ammo.
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Lastly... if reloading is anywhere near your radar screen, then you want to start picking up every single piece of cartridge brass you see from now on. You can't reload without having plenty of empty brass. It's nothing to have 500 to 5000 pieces of empty brass. And those pieces of brass you find that you don't reload can be swapped for those that you do.
Hope this helps!