Do you use some kind of Win95/OldMacOS software that does one thing (CoolEdit = mouse glitches) really cool way and is nor replicated by modern soft?
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I keep an old āhairdryerā iMac with OS9 on it primarily for Digidesignās Turbosynth and Jupiter Systems (Antares) Infinity. Turbosynth is a very old modular sound design environment aimed at creating and manipulating audio files that can be offloaded to a sampler. It can manipulate imported samples or generate sounds from the ground up. Itās all offline - you have to wait a moment for each change to take place, but nothing else sounds like it. It inspired many of todayās graphical sound design applications and was, in fact, the first place I ever saw multi-segmented envelopes, ala Absynth.
Antares Infinity was an excellent seamless sample looper and, in many ways, nothing since has bettered it. This was a secret weapon among many sample designers in ye olde days, as it could iron out normally impossible-to-loop complex sounds such as choirs and orchestral sounds. I once did a sample collection of acoustic orchestral instruments.
http://web.archive.org/web/20020604085019/http://www.antarestech.com/products/infinity.html
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Not sure if it qualifies but I still love Audiomulch.
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I still regularly use most of the old mda vst plugins, mostly because I canāt be bothered finding anything to replace them with.
I also have an old macbook with OS9 and some old software, but Iām not motivated to use it. OS9 kinda sucks for most things tbh.
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Soundforge Acid!!! Nuts the way it streched samples to the bpmā¦everything was glitched outā¦
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Vaz was my first software synth, loved it!
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Turbosynth looks amazing! Is there any decent way to run it on a modern computer, I wonder? Iām totally unfamiliar with emulating OS9 on a modern mac, but I kinda want to look into it now.
Iām not sure, to be honest. I would think it could be run on OS9 via some wrapper like Virtual Box, but Iāve never tried. Seems like TurboSynth would be an easy one to run that way, as it doesnāt require any connection to the outside world.
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I learned how to sequence and edit audio on Cakewalk Metro V on OS9. There was a bit of math involved but cutting audio with it was a lot of fun.
A lot of OS9 stuff was just plain abandoned when OSX came about. 
Acid is coming back soon
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I just upgraded to sound forge Mac 3. Man it feels like cool edit pro with the mouse gestures. I only wish it had a āsave file asā function. I donāt mind doing a copy and paste as new.