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A quick check of the Apple web site reveals that the PLW 300 only has a serial port and communicates only in Quickdraw. That means it is unlikely to ever work with Windows.
Windows XP does not list the 300 under the list of printers in the add printers program. It does list several older printers by Apple. I have a PLW NTR from the same age, and it does work becouse it is Postscript and handles PCL4+. It also has a Parralel port. Likewise it also should work with OSX as do the vast majority of postcript devices.
The reason it does not work with OSX is that it is a non networkable personal printer that uses a serial port not found on any machine designated to run OSX. Even the older Postript printers from that era with localtalk ports are a bit difficult to integrate into a current 100 baseT network. They require a protocol converter/bridge to connect the two different networks.
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