I am in a business that requires really really expensive software. I could easily spend 3k on the programs I need to be a designer, not including the computer equipment!
But I have found a way to legally purchase software for a much lower price: the student discount. At my alma mater we actually had a retail location offering software and hardware at deeply discounted student prices. How deeply discounted? You can purchase a copy of Studio 8 that will usually run you $999 for $109 or Production Studio for $365 instead of the normal $1,699. Even if your school isn't big enough to have a store there is probably a discount that you can use, you will just have to dig a little deeper.
You should definitely take advantage of these deals while you are still in school but what if you are a recent grad like me? I just emailed a friend who works at the university (I feel like I should at least plug his band for doing me such a huge favor) and he was more than happy to purchase and mail the software to me. This little secret makes previously unattainable software in the realm of reality, and in my case is helping me launch my freelance business! I am now set with all the hardware and software that I need, so I can only blame myself if I don't see this goal through.