When you buy your shiny new Olympus DS-5000, DS-5000iD (and also the DS-3400) digital dictaphone it comes with software for both Mac and Windows, in fact you get one licence for each operating system. Windows users get to install DSS Player Pro v5 Dictation Module and Mac users get DSS Player Version 7 Plus (at release 7.2.4 at the time of writing this). Both the Windows and the Mac software are similar in that they both let you play the audio files recorded on your digital dictaphone, both let you edit your audio and both let you convert your DSS Pro audio files (.ds2) to other formats.
On the Mac however, unlike the Windows software, the ability to automatically send your dictation somewhere (email to your typist, drop onto a network drive for your typing pool etc) is missing. On the Mac audio files need to be manually sent to your typist or transcription service, unless you use Dropbox.