You only have to buy the equipment once, if you do it right. It's been said many times before, regarding many items: "Don't spend too much, but spend enough."
Learn about the various presses, dies and other equipment, and keep an eye toward the classifieds. You can save a ton of money. Good reloading equipment is hard to wear out.
“At the core of liberalism is the spoiled child – miserable, as all spoiled children are, unsatisfied, demanding, ill-disciplined, despotic and useless. Liberalism is a philosophy of sniveling brats.” — P.J. O’Rourke