ProCoder is still the champ on Windows, imho.
As you already own it, I see no need for other tools.
The easiest way would be networking the two machines and setting up a watch folder in ProCoder.
On the Mac side, Episode (formerly Compression Master, recently acquired by Telestream/Flip4Mac, makers of the WMV tools you mentioned) is by far the best compression tool money can buy. Again, imho 🙂
https://www.flip4mac.com/episode.htm
Episode is almost exactly like ProCoder in terms of batch capabilities, multi-format support (MPEG 1/2/4/AVC, WMV, Real, QT, FLV, 3GP etc.)
If you only need to export to WMV, the Flip4Mac WMV Tools are perfect. They can even be integrated into a Compressor setup.
If you want or need to produce the highest quality possible there’s no way around 2-pass encoding, which is only available in WMV Studio Pro HD.
Best regards, Oliver