I'd stay away from 98, far far away.

And I'd only do 2000 if it has a real serial port.

USB devices are a headache on 2000.

Personally I'd go with XP, much more friendly w.r.t. to device configuration.

ThinkPads in general are very good.

If you get stuff that's too dated you have other headaches.

- Fiddler (IMHO)

If you think listening to music is fun, try learning an instrument.
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Computer: Foobar2000, 5K, Mojo, HiFiMan HE1000 V2