This may have been a bug in an earlier version of the software.
The app is now simply called Windows Phone and is available through the Mac App Store.
I played a track on both the Lumia 800 (WP7) and Lumia 920 (WP8) and synced back with my iTunes library (Mac OS 10.8.4, iTunes 11.0.4) and the play count increased by 1 in both cases, as expected.
Use an USB cable. Put in it your Mac and normally it'll work.
If You want to sync files, I should consider using OneDrive on your Phone and Go to http://onedrive.com/ on your Mac. If You want To do It completly Go to http://m.windowscentral.com/windows-phone-sync-app-mac-os-x-updated-support-windows-phone-81 and download the app.