You should always buy something if you can afford it. I can't afford anything so everything on my computer is pirated one way or another (except the music - gotta buy the albums). Then again I buy the music in CD format so I can say "ha, I have a disk here and I can physically hold it and I am SUPPORTING my favorite artist". I don't know anyone who would do that with a piece of software... In fact most of the pirated stuff I have I don't even use! CS3 Master Collection was the biggest waste of 3gb download ever - I don't even use a third of the stuff on there.
Fun fact: Vista was the FIRST OPERATING SYSTEM in my household that has even been legally purchased. And that's because it came with my laptop, which I then upgraded to a cracked Vista Ultimate because business was crap.