It might not be surprising to know that I'm generally OK with the fact that sometimes you have to pay for software, seeing as how I work for the biggest software company in the world. Since Web hosting has come down in price, in the middle of the last decade, software has been one of my biggest expenses. There are a few categories of big ticket items I don't have to buy frequently, or maybe not at all. One of them is the Adobe stuff.
For better or worse, Photoshop, Illustrator and the like are pretty standard tools, and I do believe they have value for what they cost. I've also used After Effects and Premier on occasion, as well as Flash. I've bought the "production premium" bundle three times in 12 years, so I don't run out and upgrade every time. I don't think that's worth it. The last one I bought was CS3, about four years ago.
CS5.5 is the current version, and it has a lot of new goodness in it, and with all of the negative press around Final Cut Pro X, they're making a sweet offer: The production premium bundle is half-price. So the upgrade from CS3 or full version comes out to $850, which is about a hundred less than the upgrade price. It's a tempting offer, because each new version means a more expensive upgrade price, until it gets to the point where you have to buy the full version.
Five or six years ago, I would've just done it, no questions asked. These days, it's harder to justify. I actually scrutinize most of the business purchases I make now, particularly after digging myself out of the hole last year. The problem I have is that I'm still kind of a sucker for good deals (like the matte box I got for my camera rig).
The half-off deal lasts I think for another two months, so I suppose I have time to think about it.