Apparently if you're me, the answer is yes.
After holding out on buying new software to cover my graphic design needs for the past nine years, I purchased Photoshop Elements last week, rocketing me into 2008. What I had been using instead of Photoshop for nine years was Metacreations' excellent Painter 3D. I never even used the 3D part of it. I just used it to simulate things like paint, pencils and crayons on screen, and perhaps more importantly it offered an awesome system of floaters (what Photoshop calls 'layers'), making for very flexible design options.
Painter stored its files in a proprietary format called RIFF. I've got nine years' worth of RIFF files on my hard drive, including the source material for all my online comics. Painter doesn't even run natively under Mac OS X, but I can still run it on my Mac G5 under Classic mode. The new Macs have switched over to using Intel processors which will enforce the kissing goodbye forever to the classic OS, so it's guaranteed I won't be able to run Painter on my next computer. And since I now have a cut-down version of Photoshop as well, and no contemporary software in the world reads RIFF files, I decided today it was time to say goodbye to them.
I felt nervous about erasing what seemed like such a mountain of my work, but I couldn't think of any situation in the future where I'd really need the files. All my comics now exist in their final versions online and I know I won't be going back to them.
Once I'd erased the RIFFs, I erased Painter itself. It was only one of two pieces of software that ever caused me to fire up Classic mode. The other one is the Mac port of the originally-for-the-3DO-console FPS 'Killing Time', and just recently I got a carbonised version of that which runs under Mac OS X. But that version still won't run on the next Intel-based Mac I own. Stupid future!
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