Mostly I was referring to the kind of shareware where it works just fine (not crippled in any way), and you are encouraged to pay a purchase fee, which is little more than a donation to the developers. When I pay that fee, I am just saying thanks.
Let's look at the other side. I know tons of people who go to a gnu ftp site and just download away, greedy for free software. These people never write articles or help newbs or even say "thank you ever so much for your time" when posting to a support mailing list. So free/open software doesn't automatically make a good community. I help out where I can because I appreciate all the people out there who helped me out. I would be lost if it wasn't for kind people at gcc, libpng, and mozilla. I want to return the favor. But not everyone is righteous or just when it comes to the computer.
Anyway, you do what you can to help out. I don't see anything wrong with paying for software, if it is good and reasonably priced. $130 for OSX, $100 for Illustrator CS (educational!), these are investments I am willing to make.
Ah, capitalism. Well, as long as we are stuck with it, we might as well do the best we can with it.